Midway upon the journey of life, I found myself within a dark wood, for the straightforward path had been lost.

I took a course in college called ‘Great Books’, where the professor — a tall, emphatic lecturer already famous at the UM — talked extensively about the meaning of this line, the first line of Dante’s Inferno. Most believe the line is a setup for the narrator’s journey through the Inferno itself. This professor, however, had a different interpretation: it was an allegory for how Dante himself felt at that stage in his life — middle aged (at 35!), exiled from the city he loved, grappling with his own demons.

Throughout my own life, I also at times found myself in a dark wood. At the same age as the narrator — 35 — it became clear to me that I wasn’t the best I could be. Dealing with the emotional challenges of a startup and the daily attempt to juggle a demanding work environment with the everyday commitments required to be a present father and husband were taking their toll.

So at the beginning of 2015, I embarked on a journey with a simple — but by no means easy — goal: to be happy, and improve the lives of those around me (while still being effective at work and home). I changed my reading habits, picking up self-improvement & self-help books that I previously would have dismissed as hokey and treated with cynicism. I started learning eastern philosophy, practicing meditation and reading all of the articles on mindfulness I could get my hands on. More recently I started experimenting with diet to maintain consistent, healthy energy throughout the day.

I also started talking to others in similar life stages about their approaches to similar challenges. Quickly I discovered that I was not alone. I started to collect best practices from the people that I would meet. I realized that if so many of us are coping with the same challenges every day, it would be a valuable resource to make these daily practices exposed & available to others, too. The wisdom of the group always trumps the wisdom of the individual. Thus, the balance was born.

The balance is an interview series with a handful of people every month — high achievers with demanding lives who are always trying to get better. We discuss their daily routines, & how they achieve happiness and balance. I’ve borrowed inspiration from influential books such as The Power of Full Engagement, podcasts such as Jerry Colonna’s Reboot and long-form interview series such as Om Malik’s Pi.co (with, as I’ve since learned, a strong dose practical effectiveness tips a la Tim Ferriss). I am publishing these interviews on Medium, and also trying to learn how to develop a following for a small passion project.

Earlier this year, I read a book called The Art of Communicating, by Buddhist author and activist Thich Nhat Hanh. It was an insightful read on a compassionate, mindful approach to everyday communication at home and at work.The goal of communication is to be understood by others and understand what others are seeking to communicate. But it’s so easy for this simple idea to be derailed. 

Firstly, technology often gets in the way. I’ve been guilty many times of flipping open a laptop to check or respond to quick email, or receiving and responding to texts and IMs on a mobile device. Not only to these interruptions immediately rip you out of the present moment & break the communication flow, but they also signal to the communicator that ‘I have more important things to do than be in this conversation right now’. If this is really the case, there’s little point in speaking in the first place! Every worthwhile conversation deserves full attention. I try to take technology out of my meetings and conversations entirely, unless I am in the midst of an urgent situation that requires me to be on standby. 

Secondly, in conversation we have the tendency to compose our own responses in our heads while someone else is talking, or for our minds to wander off topic completely. This tendency is completely normal and human - however it also stands in the way of the goal of a conversation. It also isn’t the kind of empathy you’d want extended when you are speaking. Borrowing a trick from meditation, when this happens I try to recognize that its happening, and bring my mind back to the conversation. I also bring my attention to my breathing.

Deep listening and right speech

Nhat Hanh talks about the two key elements to compassionate communication: deep listening, and right speech. 

Deep listening

Deep listening is listening to the other person with the only intention of relieving the other person’s suffering & making them feel better (suffering is a very Buddhist word but the principle behind it is what matters). This means listening fully, not interrupting and suspending judgement - not wanting to inject our own views or point out where the other person is misguided. Only then are we in a position to respond fully to the other person. If this idea seems a little too Buddhist for the workplace, or not every quick exchanges don’t allow for this kind of patient communication, I still find it to be an empathetic method for framing the right way to listen vs. respond in a particular situation. 

Right speech

Nhat Hanh talks about 4 guidelines to right speech, derived from Bodhisattva teachings: tell the truth, don’t exaggerate, be consistent / no double talk, and use peaceful language: 

Tell the truth - at a basic level, being truthful establishes an irrefutable pattern of trust with others, which is a fundamental building block of any healthy relationship at work or home. As soon as any doubt exists in a truthful relationship, everything is in doubt. 

However, telling the truth for me goes beyond its straightforward definition. As Kim Scott talks about in her article ‘Radical Candor’, I consider telling the truth being truthful to the point of entering into sometimes uncomfortable territory of saying what needs to be said in order to make the individual or team better. This includes pointing out areas of development on the spot (if you are thinking it, you should figure out how to say it). 

However, its important to always maintain empathy and have a ‘radically candid’ discussion from a place of trust - as Nhat Hanh says, if the truth is shocking we need to find a skillful and loving way to say what needs to be said. For this reason, real truth telling requires a lot of practice. 

Don’t exaggerate - there’s a tendency to exaggerate in the workplace, where emotions can run high and data is often ambiguous. So, in order to make our point sound more credible or win the argument, we sprinkle in something that isn’t quite true, or at least we don’t know for sure that it is. Exaggeration erodes trust and stands in the way of effective communication. It’s okay to feel things and not only speak from fact - however this means labelling feelings and ideas rather than presenting them as facts. 

Mike McCue also talks about critical decision making from a position of fact in ‘The Most Powerful Lesson I’ve Ever Learned In Business’. Slightly off topic, but worth a read. 

Be consistent / no double speak - this refers to communicating different things to different members of the team about the same topic as a way to try and control the situation (or maintain some sort of information advantage). Double speak is both taxing on the individual as well as the organization. For the individual, maintaining multiple versions of who we told what to takes up brain power than can be used for more productive activities. For the organization, this can cause division in the ranks (e.g. this person tells me things he doesn’t tell you). Of course, this needs to be appropriately balanced when it comes to sensitive items, but for the majority of organizational information should be equally accessible across the team. 

Use peaceful language - any speech that is ‘violent, condemning, abusive, humiliating, accusing or judgmental’ absolutely has no place at work. As Nhat Hanh says, when we speak in a way that causes tension and anger, we are nourishing violence and suffering. I would add trying to tone down strong or overly assertive tendencies in communication, as if any member of the team feels intimidated, its an environment where not all facts will be shared freely and openly. 

Yesterday I had the pleasure of sitting on a NewCo panel, moderated by David Mandell of Pivotdesk, about building and maintaining company cultures. One interesting conversation developed around the familiar startup philosophy of ‘hiring slow & firing fast’. I agree with this approach broadly, but I also think its subject to really easy oversimplification or misinterpretation. So here’s how I think about it.

I don’t necessarily hire slow, although I do ensure that I go through the process of defining the organizational need for a specific role upfront, with a clearly written job spec to match that articulates (to the best of our ability) my view of the skills required for success. Once this is put in place, hiring may happen very fast, or it may be very slow - it all depends on how quickly a candidate surfaces. When we see what I like, I tend to hire very quickly. For this reason, I’ve always treated candidate short lists with some cynicism - find me one great person that meets the requirements I’ve articulated, and I’ll won’t hesitate to pull the trigger! And of course, when in doubt, don’t hire. I talk more about hiring process in my Empowered Hiring post. 

On firing fast: the question isn’t how quickly to act when there’s an obvious personnel problem - the question is when is the personnel problem obvious, & how fast is fast enough? I came out more conservative than the panel on this. In my view, you can’t make a decision as serious as a termination without separating facts from emotions. And while there’s often a compulsion to fix the situation with immediate action to make ourselves feel better, taking a few more days or weeks to make an appropriate, balanced decision is only fair to the individual in question (& the broader organization). After all, it might have taken months of time to get who the hiring manager believed to be the right person in the room in the first place, following a well-run process and organizational commitment. Jerry Colonna articulates this tradeoff well in his post ‘The Gift of our Ambivalence’. None of this obviates the need to act quickly for egregious performance issues or gross misconduct. 

The best way to establish a productive & stress-free relationship of any kind is to set the right expectations. But it’s tempting at times not to have the discipline to appropriately set expectations at the beginning. I’ve experienced the anxiety of mis-setting expectations on the receiving and the giving end, which has led to a lot of discipline with my own expectation setting.

Good expectation setting examples in the real world

For customers.

At onefinestay, we try to set expectations at the onset for how a customer is likely to experience the service. This doesn’t mean playing to the edge cases - but what we genuinely believe is likely to happen in the host or guest experience. For the host, who is offering their home to guests while their out of town, this means investing the time upfront to ensure understanding of wear-and-tear, what happens in the event something goes wrong in the home during a guest stay, and how we respond - timelines, who pays - should that something actually cost money or time to remediate. We also try and set expectations to the best of our ability around likelihood of bookings at various price points and times of year. This means investing the time up front to present hosts with actual data from our business (e.g. if you live in a 3-bedroom in Chelsea and will be gone this summer, we will pull comparable homes from both the market and our own internal host community and speak to performance - and leave this behind after our first meeting) so an informed choice can be made. Hosts are always evaluating an alternative, even if it’s just leaving their home empty, and we only want to enter into situations where we believe we can provide the killer product. 

For guests, this means doing everything we can prior to the booking and arrival stage so that they know what they’re buying. We’re building out a new accommodation category - a home with hotel-style benefits, so sometimes expectation setting is as fundamental as ‘be aware - you are booking a real person’s home!’. We also try and list all of the home specific quirks transparently on the home listing page in a ‘home truths’ section - if a cat lives in the home and you have allergies, you’ll know this upfront.  

For hiring.

Jerry Colonna says that what employees need most to succeed is clarity. Amongst other things, this means a well written job spec that reflects the actual work required for the role. I try when interviewing to ensure a prospective hire knows what they are getting into by asking ‘what’s your understanding of the day to day role’? Lastly, it’s really important to talk about how things like typical office hours, expected out of hours responsiveness, promotion, and pay cycles work within a specific environment - this varies a lot between organizations so is best to expose fully. I can still remember countless evenings when I was a banker, work done for the day, not knowing whether or not it was OK to go home and get some rest.

For special cases, I loved Sheryl Sandberg’s story in ‘Lean In’ about Cynthia Hogan, who was asked by Vice President-elect Joe Biden to join his staff after taking time off to have kids. Instead of declining a role due to her presumption of the late nights required, she flagged this as a concern early to which Biden responded ‘well, you have a phone and I can call you when I need you after dinnertime’. Cynthia exposing her situation upfront led to her boss resetting his own expectations so he could bring in the right talent for the job. 

For investors.

Do you know the return or liquidity timing expectations of your investors? Even within the VC world, I’ve observed a surprising amount of variation in investment performance expectations - some funds will steer the business towards ‘$1bn or bust’ outcomes, whereas others would prefer safer bets for more conservative returns. Some funds are investing purely to maximize financial return, others have non-monetary objectives. And, fund lifecycle will play a big part as well - are you the last deal in an aging fund with a lot of unrealized investments or the first deal in the next fund with a proven track record? This more than most other aspects of business can dictate strategic options down the line. 

For suppliers.

For suppliers & service providers, discussions often get mired in complicated contracts drafted in legalese. This can make the more human challenge of expectation setting more difficult. In some cases, contracts can be modified to reflect the intent of the agreement. If not, I always establish a clear ‘plain English’ understanding, in writing, of how I expect things to unfold if not everything goes as planned, and ask for confirmation of agreement in writing, too. Or I find a supplier with a more robust contract. At onefinestay we’ve found this particularly valuable with maintenance providers - e.g. plumbers, exterminators, general contractors. It was illuminating to contrast what certain suppliers would say over the phone vs what they’ll agree to in a contract. 

Causes and remedies

In my experience there are two root causes of mis-set expectations - one innocent and the other more insidious. The innocent cause of mis-set expectations is a misunderstanding - language is complicated and conversations can often conclude without both sides in full agreement. To combat this, I often find myself repeating certain salient points to underscore their importance (even at the risk of redundancy), and sending an email recap afterwards. I also always try and practice what Thich Nhat Hanh calls ‘language of the world’ - when in doubt, use the simplest word or phrase possible to agree a point. Good communication is about understanding, not demonstrating an advanced command of a language.  

The second root cause - and one that I’ve certainly fallen victim to from time - is a glossing over specific details because of fear losing the ‘deal’ - the investor, the hire, the revenue. So we kick the can until a future day of reckoning, when either we get lucky because an outcome we’ve alluded to comes to fruition, or things fall apart and we have to pick up the pieces. Needless to say: this isn’t a good outcome for the expectation setter and can leave a permanent feeling of disappointment with the other side. It’s also a great way to stress yourself out in the meantime, which isn’t a good way to live. There are a number of personal development strategies for dealing with fear. And as my old boss used to say, part of the battle is being completely comfortable with any potential outcome so that you’re not afraid to lose the deal - whatever that deal may be. 

Parting thought 

Lately I’ve been trying hard to provide clarity and certainty in my interactions with friends, family & colleagues. This practice began last year when I was documenting email best practices for my ‘sending good emails’ post - for example, when I receive an email with an action for me, I’ll send a quick one-liner response - e.g. ‘got it - will get back to you by end of day’, or ‘noted’. As I’ve started to think more about this idea, I’ve realized that providing insight into my thought processes applies to many other situations I encounter on a regular basis and can help the person on the other end of the interaction. Some of this thinking was codified by Jerry Colonna’s interview with Duncan Morris on the Reboot podcast.   

One example of a common situation: a colleague in a professional setting poses a hard question that is going to take me a few days to work through. Rather than starring the email and revisiting when I have some headspace, or responding vaguely e.g. 'let me think about this’, I am trying to be more specific - e.g. ‘that’s a challenging question and I don’t want to answer off the cuff - how about I think about this and get back to you by Friday? Alternatively, if you’d like my ‘gut’ reaction now, happy to provide'. 

This practice can also be applied with interactions with family - for example, if my daughter Alice asks me to play with her but I’m unable to in that moment, rather than saying ‘not now’ I’ve been trying to be more specific: ‘Lets play in 10 minutes after I do x/y/z’. Hopefully this extra bit of certainly removes any potential stress or wondering when I am going to be available, and frees her mind to focus on more productive thoughts.   

An example of this playing out in a different way is with Danny Meyer’s ‘Hospitality Included’ - removing any stress or drama about tip levels for servers by baking gratuity into the bill across USHG’s restaurants. I was moved by stories of waitstaff crying at the end of the night & would imagine it’s had a strongly positive effect on organizational mental well-being. 

Heading into the new year and thinking about 2016, I decided to do a look-back of all the content I read and listened to in 2015.

In 2014, I dove headfirst into the business memoir - personal stories of entrepreneurs, their management philosophies, and company growth. This is a genre that resonated deeply with me, and helped shape the way I think about leadership. I found the stories of business leaders such as Danny Meyer, Chip Conley & Howard Schultz to be inspiring and engaging, and the perfect supplement to more foundational business books such as Good to Great.

Towards the end of last year, however, I was seeking a change. As someone who loves history in particular, its always been a regret of mine that I didn’t take more history courses - or explore liberal arts more broadly - when I was in college. So early in the year I started reading and listening to lots of classical history. One enabler of this was Audible’s addition of Great Courses content - college-style lectures on sweeping topics such as ‘The History of Ancient Rome’. I ended up listening to three 48-lecture series on classic civilization: Daily life In The Ancient World, The History of Ancient Egypt, & The History of Ancient Rome. I also read a new history book on Rome - SPQR - as well as a book on the historical Jesus (Zealot) and a travelogue set in the ancient world (Travels with Herodotus by the late Ryszard Kapuscinski).

Some of this was a lot of fun. However, looking back, its disappointing to me that out of the hundreds of man-hours of reading and listening I’ve actually retained very little. I can’t remember a single thing beyond names from Travels with Herodotus (although this coincided with the birth of my second child, so perhaps I’m being too self-critical), and I only have a hazy recollection of much of the Great Courses content. Perhaps I’m not as interested in history - at least in this stage of my life - as I thought I was, or perhaps I just need to consume history in a different way - e.g. visually through documentaries and museums. I also think chronological history probably isn’t my thing - when the history was more narrative my retention was far higher.

There were some highlights, however. I read Lean In, & would recommend it to everyone. And a quick and great read was The Internet is my Religion, written by entrepreneur Jim Gilliam, about the connective power of the Internet against the backdrop of a fundamentalist Christian upbringing, loss of a parent to cancer, and cancer survival himself. Over the summer I also decided to re-read one of my all time favorites, Thomas Pynchon’s Mason & Dixon, partially as a challenge to myself to see if I could do it. With family & startup responsibilities, my life isn’t exactly conducive to tackling an postmodern 800 page book written in 18th-century prose. I’m glad I got through it, and recommend it for anyone looking for a surreal, historical novel about pre-revolutionary America by one of the best all-time authors.

I also read a book that was life-changing. 10% Happier by Dan Harris is a readable introduction to the teachings of Buddhism and meditation. The power of the book was Harris’s ability to lead me on an emotional journey of self-discovery where the story arc leads to incorporating Buddhist practice into daily life. It was a great trojan horse - I’m not sure whether I would have been as open to education about Buddhism and meditation practice any other way.  I intend to read more about applied Buddhism and spirituality in 2016, and subscribed to Triangle magazine to kickstart the year with some of their content.

Over the past year I’ve also stopped switching between reading book & audiobook, as I had highlighted in my post ‘Reading Books 2.0’. My tentative plan for listening headed into 2016 is to move to fluffier audiobooks where missing a detail here and there doesn’t really matter, as well as try out some new podcasts. I haven’t quite figured out the optimal way to mix audiobooks with the voluminous amount of podcast content into a cohesive listening library, but I’m going to try. I just started Jerry Colonna’s Reboot podcast and have been enjoying it immensely, so am hopeful that keeps me busy for a while.

In terms of reading goals for 2016: I am starting the year focused on self-improvement, self-discovery & ‘applied’ spirituality (e.g. the teachings of Buddhism, Judaism, and other spiritual or religious disciplines to modern life & leadership). I started a book featured in Amazon’s ‘Customers also bought’ section of 10% Happier called the Gifts of Imperfection. Other samples downloaded on my Kindle: Choose Yourself, The Art of Communicating, Soulcraft. I also want to tackle the 7 Habits of Highly Effective People once and for all (I’ve had several stops and starts) - same with Victor Frankl’s Man’s Search for Meaning. Lastly - as with listening - I’d like to figure out the right way to incorporate blogs and articles into my repertoire. I find that I skim this content during the day at my desk and retention is very poor. I’m trying out the app Pocket with the hopes that it can be my knowledge base.

Sending good emails can be the most effective way to communicate across an organization. But it can also be one of the most value-destructive & efficiency-killing activities when wrong. Modern methods of communicating - e.g. quick one-liner iPhone responses with autocorrecting - only make organizations more susceptible to bad emails. 

Sending good emails at its core is all about empathy, and will make your organization run more smoothly by not wasting time trying to interpret email meanings, not being unnecessarily overly looped in, and not spending time actioning the wrong thing due to poor word choice. 

Here are some email best practices to ensure we’re sending good rather than bad emails.

Email basics: use of to, cc, bcc, subject fields

to: who the email is being specifically sent to and you are expecting a reply from. This should then be reenforced in the body of the email - e.g. ‘Hi John, (Jane, Jim on cc)’

cc: people who need to be aware of the content of the email, but do not need to respond

bcc: people who need to be aware of the email, but for various reasons the sender doesn’t want to expose this to the group

subject: keep the subject a concise description of the topic at hand. If the topic morphs or changes over time, take the lead in changing the subject, too

Both the to and cc fields should be kept as short as possible. If you aren’t sure who to include, do some research beforehand to see who should be accountable

When adding people to an email string, include a (+ John); when subtracting, a (- John)

Body format and reply convention

Internal email communication is not prose - its technical communication designed to resolve an issue, inform others more efficiently than an in-person discussion, or recap what’s been agreed following a discussion or meeting. Spend as little time as possible trying to make your email ’sound good’, and reinvest that time in careful word choices to remove an ambiguity from the message. Organizations should set the expectation that terse or direct internal communication is acceptable, encouraged and free of judgment, as the goal for internal email is extreme clarity and intent. And less time composing internal emails frees up time for higher value activities.

The recipient of the email (e.g. who was in the ‘to’ field of the email) should formally acknowledge receipt and confirm actions - e.g.

‘Got it - I will call Joe'

And once the task is completed, a further email should be sent to recap, and put the issue to bed - e.g. 

‘Spoke to Joe. This issue is now resolved - thank you.’

If you as the sender haven’t received this confirmation, its still your problem - stay on top of it until its confirmed that this has been firmly picked up by someone else.

If in doubt on whether or not you should reply (if you are cc’ed / not directly referred to), ask yourself:

‘Do I have something to say that is going to add value to this discussion?’

If not, best to sit on the sidelines.

After a decision on a specific issue has been made, have the self-discipline send around a recap email with what’s been decided. It always surprises me how much time is spent going back and forth over email or in-person about an issue, but the final step of solidifying a decision with a recap isn’t taken. Establishing a clear, final paper trail is important.

Some other tips that I use for effective emailing & communication

Try and keep one email per topic, with a clearly corresponding subject. Multiple topics embedded in the same email often leads to too many recipients on the email and unclear actions. I will often send successive emails to the same recipients with different topics and subjects to keep issues separate.  

Reread your email before hitting send and ask yourself: am I being as clear as I can be? If sending an email on the go, make sure your phone hasn’t autocorrected any words that the recipient is going to be confused by.

Hiring is the most time consuming and important activity any organization undergoes. Anyone running a business should consider themselves the ultimate ‘head of talent' (despite the benefit of bringing in senior HR leadership as the company scales). However, best practices around the various stages of hiring in my experience are not universally well understood or followed. Since most of onefinestay NYC’s hiring needs are at entry level, that’s the topic of this post.

Setting the stage

Entry level hiring is challenging because there’s a limited amount of hard experience for someone only a few years out of school - and soft qualities typically matter more than hard. At onefinestay, we find future leaders are best groomed, not hired, and more times that not come from within, making entry level hiring critical to long term success. We see thousands of resumes a year, and educational pedigree or first job rarely tells a complete story. Some of the things we look for beyond the resume are early signs of leadership and work ethic - did you work throughout high school or college, did you have a hand in helping shape a local business in your hometown, etc. More on this below. 

Currently at onefinestay NYC, we’ve decided not to centralize hiring to a ‘head of talent’ or recruiting manager and keep responsibility with team leads who act as hiring managers. This is because one of the key skills for managers is to know how to hire themselves - bringing in a high momentum new hire from spec to close is one of the key indicators for any hiring manager that they are ready to be managing a team.

Stage #1: Writing your spec

It’s always critical to write a job spec, even if the hire ends up coming from within the company (in many ways especially if the hire ends up coming from within the company). Writing a spec is the essential forcing mechanism for the manager to think through the specific skills and qualities they want to add to their team. I’ve seen many hiring processes start with a fuzzy spec, and then the role eventually molded to the specific skills of a specific candidate, rather than the needs of the organization. Putting it all down on paper in a structured format is also the cardinal exercise in expectation setting between the hiring manager and the candidate, and provides hard criteria to test against in an interview setting.

Here are a few other tips for spec writing: 

Set a few ‘non negotiable’ hard qualities or skills that are identifiable from a resume to help narrow the hiring pool and focus on what’s essential for success in the role. Otherwise, the time spent screening and bringing in qualified - but not home run - candidates with have amplified effects downstream, mostly on the hiring manager’s (already scarce) time.

Write a spec using easily understood, externally-facing language. Every   organization has a way they present themselves to the customer-facing   world and their own internal way of speaking. However a spec isn’t the right venue for a brand overdose. I believe the role of a job spec is to attract the best people by attracting interest from as wide a pool as possible - period. Cultural and organizational fit can assessed throughout the hiring process.

Have a few different titles in mind. It always amazes me how a job title     influences candidate propensity to apply. Some people prefer whimsy e.g. ‘Jack of all trades’, others ‘hard’ titles e.g. operations coordinator. The title and perhaps even the first paragraph should be split tested in the sourcing process - candidate acquisition in the digital world isn’t entirely different than customer acquisition.

Stage #2a: Sourcing

Unless you are Google or Facebook with enormous inbound flow from the best and the brightest, chances are the way you advertise your spec is going to be the most critical success determinant in the process. Alongside the right kind of spec, our goal when sourcing is to address the largest possible candidate pool, and it's our job to be clever about how to whittle it down and find what we’re looking for. It’s not particularly difficult to ensure your spec has the widest possible distribution, it's just an often overlooked or neglected part of the overall process. It’s tempting to put a spec on the /jobs page and watch the applications roll in - the reality is in my experience most of the best talent needs to be proactively hauled in.

For entry level hires into the NYC business, we’ve found that college job boards, Craigslist, and startup specialists like HireArt & Lynxsy yield the best results. It’s amazing to me how many great people are still looking for jobs on Craigslist - and it’s an instant response channel. Average quality is low, which places even more emphasis on screening, but in our experience some of our best people found us through this channel. It’s also a channel that requires regular maintenance; just like Google ads or eBay listings, placement matters a lot and as soon as you’re on the second page of listings conversion drops off dramatically. Posting on college job boards is time consuming, so we typically choose a handful of schools that we’ve had success with in the past - often ones where there’s alumni active in the organization. Focusing on a few schools also allows us to build relationships with the career services offices, who can often be helpful agents and direct the right type of people our way.

We were an early client of HireArt, who has a great approach which subscribes to the ‘wide pool / whittle down’ framework. They distribute job ads through all of the main recruitment sites as well as university job boards, and funnel applicants through a fairly intensive video screening process. We’ve found that this saves precious screening time and gives us highly qualified candidates. The question we’ve had about this approach is whether or not we are creating too much of a hurdle to apply when the candidate hasn’t yet been properly introduced to us.

Lastly we’ve created a profile on The Muse, which gives us a venue to showcase our office and culture and has generated lots of inbound interest. 

Stage #2b: Screening

After you've ensured your spec is being seen by a wide audience, time to focus on screening. A hiring manager’s time is always scarce, and spending tons of time screening can be a huge time sink. So besides figuring out which qualities are non-negotiable, I typically have candidates write a few simple paragraphs answering some basic questions - why onefinestay, why this role in particular. I don’t generally read cover letters as I find them to be too ‘form’ and unspecific.

Specific written communication not only begins to probe motivations and depth of thought, but is a great way to see the quality of written communication and attention to detail - e.g. any typos or obvious grammar errors in an email sent on your own time doesn’t bode well for composure in the heat of the moment. We’re a business that prides itself on clear customer communication, so this is a great indicator.

To capture this information without revealing specific email addresses - which can lead to a lot of unnecessary email traffic for unqualified candidates, I typically include link to a Wufoo survey at the bottom of the spec that allows the candidate to attach their resume and answer basic questions.

Stage #3: Managing the ‘CX’

Does your organization care about customer experience? Then you should also really care about 'candidate experience' - well-run hiring processes lead to the right employees which lead to a natural focus on great customer experience - it's all a continuum.

A few important call outs:

Choose your interview panel carefully. Ideally it should be a mix of decision makers (peers, sign-off superiors, etc.) and culture 'promoters’. Be clear about everyone’s role in the process, and ideally have the individual team members probe specific areas that they have a unique talent in. Your panel is also an excellent opportunity to transparently showcase the caliber of talent already in the organization.

It's the hiring manager’s job to chaperone the candidate through the in-person interview process, both on the day and after - not the office manager or anyone else. This is a unique opportunity to build rapport with someone you are potentially entering a long-term relationship with. Make them feel welcome, be hospitable and sensitive, check in with them throughout the day, and ‘tail’ the day with a coffee / beer / walk around the block as the situation permits. Also dead time sitting and waiting between interviews is a real momentum killer - if this is unavoidable, have the courtesy to provide the candidate with some company information to read, invite them to take a walk, introduce them to a team member not on the panel so they can learn more about the company, etc.

If you have an open plan, buzzy office: take advantage of it. Don’t usher the candidate too quickly into the 'interview chamber'. Grab a coffee with them, allow them to get a sense of the office culture and vibe. Ideally     the candidate leaves with an idea of what it’s going to feel like to work     here.

Startups need creative problem solving. If your candidate asks for an office address when it's publicly available on the website, or doesn't know anything about you when you have an up-to-date LinkedIn profile, this doesn't bode well for resourcefulness in the future.

How I like to interview

I subscribe to the David Rosenblatt interview school - I want to understand as much as I can about the motivation of the candidate and what’s led to the decisions they’ve made - which university they chose, what they thought they wanted to do in college vs what they’ve actually done, how they decided on the career path they’ve pursued to-date, and why onefinestay is the next logical step on their journey. I want to understand what specifically they want to get out of the experience, and whether we as an organization can help achieve those goals for a mutually successful, long-term partnership if expectations are met on both sides.

An extra bonus for me - can the candidate add something new and distinctive to the organization so we are constantly expanding and extending our capabilities and knowledge? This could be directly relevant to onefinestay e.g. intense thoughtfulness around customer experiences, skill based e.g. speaking a language that no one in the office speaks (which has come in handy in all sorts of strange ways), or a specific area of knowledge or talent that it’s going to enrich the office environment. It’s a good proxy for the individual being able to expand their circle of influence and emerge as a true future leader.

Referencing

Any questions remaining after the interview process can be addressed in referencing - which is a sub-topic in its own right that I plan to address in a future post. In my experience, referencing is a rare opportunity to complete the picture of a candidate prior to joining, and provides a roadmap for candidate development and a mutually successful reporting relationship. Referencing should be run by the hiring manager, and treated as a critical part of the process, not an afterthought.   

Stage #4: Closing

Like the rest of the process, closing is no one’s job besides the hiring manager - although this is often a great time to get the founder(s) / CEO involved. Any great candidate is going to have alternatives, so ensuring that you are best positioned for success requires care and attention.

Here are a few pointers for maximizing probability of success at the closing stage. 

Directness & honesty - part of any closing process should make the candidate feel good - after all, they’ve made it this far. However it's also another opportunity to expectation-set and provide valuable feedback that should be addressed should the candidate join - without overdoing it. Realistically, in most companies it's going to be many months before there’s a formal review cycle, so regardless of the outcome it’s a great opportunity for the candidate to hear feedback from their process. It’s the first step in a transparent relationship for both sides.

Offer fairly - getting someone ‘on the cheap’ is a false economy. If the candidate works out, they’ll quickly ingrain themselves in the organization - at which point they’ll talk to their colleagues and find out anyway. Have fair, non-candidate specific pay bands and justification for comp packages at every level.

Give your time generously - committing to a job is a high opportunity cost decision for both sides. Make yourself available for further questions, sell discussions, & whatever else it takes to ensure there’s full information on both sides.

But, time is not your friend - I don’t believe in short-fuse exploding     offers, but nor do I believe hanging an offer out there for weeks. If     you’ve run a proper process and given an ample amount of exposure to the organization and yourself, the candidate should really know (assuming fair market offer) whether they ‘want it’ or not. A few days or a weekend should be enough time.

Every few months at onefinestay NYC we have a book club, and the most recent book we discussed was Good to Great. If you haven’t read it and only can read one business book this year, this would be my pick - its foundational and many other business books describe different versions of similar concepts. I actually listened to the audiobook, read enthusiastically by author Jim Collins himself (who spent 5 years with a team of researchers compiling the data for Good to Great) - in this case, listening was a great way to consume this book and make it stick.

Our discussion centered around a few specific ideas from the book - this is part book summary, and part summary of our discussion. Here were the key points:

Good is the enemy of great

In many ways, truly understanding the meaning of this line is the most important lesson in the book. It’s all about the power opportunity cost: businesses don’t become great not because they are bad businesses, but because they are above average businesses - and this prevents greatness. Being ‘good’ is probably worse than being ‘bad’ - as good is insidious & results in complacency. As J.K. Simmons says in Whiplash, there are no more dangerous words in the English language than ‘well done’.

This concept can be applied to most areas of an organization - here’s a few that we thought were relevant to us:

'Good' employees prevent companies from hiring 'great’ employees. It’s critical to think carefully about every seat in the company as an opportunity to bring someone in to the organization that can be transformational and help shape the future. It’s fine if not every employee falls into the ‘great' category today - but it should be a conscious decision if they aren’t. The construct I personally use is: are they great, or do they have the potential to become great? If neither, that seat should be freed up for someone with that potential. No matter how big the company, most of the available game-changing talent is still on the outside of the organization.

‘Good’ customer experiences prevent ‘great’ customer experiences. New brands are built from evangelists, not averagely satisfied customers. If the phone isn’t ringing or you aren’t hearing from customers, that doesn’t mean that everything is going as it should be. There may be (much) more that you can do to create a world-class customer experience.

First who, then what

‘Great’ companies featured in the book all took talent very seriously - more seriously than company strategy, at least in the beginning. And not just getting the right people ‘on the bus', but getting the wrong people ‘off the bus’. Part of the power of getting the right talent mix in an organization is the leverage it creates, as the ‘right’ people are self-motivated and mostly self-sufficient, so staff management challenges are reduced or eliminated. As Jack Welch says,  'I hire people brighter than me and get out of their way’.

Some other features of this philosophy:

Specific knowledge and skills are teachable traits - the right attitude, work ethic & dedication are much harder to come by.

Don’t weigh down ‘achievers’ with underachievers. Good employees prevent great employees.

Non-negotiable hiring rule: avoid selfish, negative or egotistical people.

Bias is: promote from within, which reinforces core company values.

When in doubt, don’t hire

The onefinestay team thought the following characteristics meant we had the right person on the bus:

Have an opinion. This specific lesson was ingrained in me from my first job as an investment banker, where one of the MDs after each meeting would turn to the most junior person in the room and ask them ‘how do you think it went?’. Many times when I am asked what I think about something, I'll respond with: ‘what do you think?’. It’s critical to have thinkers at every level of an organization who don’t outsource the brain to the boss, otherwise everything ends up flowing through the boss which results in not enough organizational leverage. With the right people on the bus, its as simple as setting the right behaviors around asking questions and options. Don’t ask for help if you could reasonably figure it out for yourself.  

Bring excellence to daily tasks - regardless of circumstances. A good example is our photographers - bringing the same a-game to every shoot, not just the magazine covers.

Seize opportunities above and beyond the ‘day job’. The job you are given is nothing more than a platform to expand your circle of influence.

Have a positive attitude and spirit of joy and contribution.

Confronting the brutal facts

This is all about creating a culture of transparency, so that information (and problems) flows freely through an organization. Charismatic, or overly strong-willed leaders are often the biggest culprits when there’s a lack of transparency in a company. Here’s how to do it:

As a leader: lead with questions rather than answers, rather than having the answer and spending time motivating everyone else to follow you. Part of ‘leading with questions’ can be implemented with one-on-one meetings with direct reports. I think Ben Horowitz has the best guidelines to how to run a one-on-one meeting, here 

If you do have the answer or a non-negotiable opinion: be clear about it. Otherwise, engage in honest debate

Clinically analyze mistakes, but do so without blame

Build in ‘red flag’ mechanisms. Everyone in the company should be able to pull the andon cord 

Hedgehog concepts

Companies that achieved greatness in Good to Great did so by simplifying their business to 'one big thing’, and organizing all of their entire business around delivering that big thing. Having a hedgehog concept is all about creating singular focus and not getting distracted by initiatives unless they reinforce that focus. Arriving at this concept is often a multi-year journey and starts with figuring out what you can be best in the world at, what you are deeply passionate about as an organization, and what creates economic value. Critically, Good to Great companies did not say 'lets get passionate about what we do' - rather 'we should only do things we are passionate about'.

It’s hard to figure out what your company’s hedgehog concept should be - we certainly didn’t solve it in an evening. But a lot of the power of hedgehog concepts for me is not necessarily figuring out exactly what the big thing is - but bringing a natural focus to business building decisions. For example, at onefinestay we’ve chosen to focus on certain types of homes with in certain neighborhoods in the city. Having a clear idea on what we’re looking for has enabled us to get tightly focused on sales and marketing strategy, messaging & hiring decisions in our home teams.