Sending good emails

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.
  • Email is an effective way of communicating - until it isn’t. If the email is escalating to an emotionally-charged place, or the issue at hand is becoming too intricate, take the communication offline (person or phone). And then send a email recap.

Empowered hiring

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.
  • End on a high & don’t overextend - when negotiation ends, make sure there’s a good taste left in everyone’s mouth and that you haven’t agreed to things you realistically can’t deliver. 

Good is the enemy of great

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.

There’s a lot more in the book that’s beyond the scope of this post. Beyond the book itself, Jim Collins maintains an online knowledge base that expands on some of his key ideas from this book and his others.