My “User Manual”

h/t to Zack Rosen and Brad Feld, I was inspired to write this after reading Zack’s user manual, which was inspired by this post from Brad Feld. This “user manual” explains the why. Why I think, react, work, and generally ‘do’ most things I do, instead of just experiencing the ‘how’.

Why are you writing this?

I’m a first time CEO of a fast-growing company with dozens of employees. I’ve made many mistakes and will continue to make more. I care deeply about being the best CEO I can be, though, I truly feel I have the most to improve on in our organization. This “user manual” should make it easier to work with me.

For context, we began 2015 with 11 Diplomats (employees at our company, Ambassador) and ended with nearly 40. It was fun. It was stressful. I made a lot of mistakes, we’re still paying down some of the ‘culture debt’ as we close out 2016. A key learning was that ‘communication by osmosis’ doesn’t scale. Expectations of what makes a great employee and/or leader in our organization wasn’t clear enough. Communication begins at the top. I screwed that up and it’s 100% on me.

This post should give potential (and current) employees a view into my thought process, expectations and culture at Ambassador. It’s the first step in more clearly communicating our expectations to all current and potential diplomats.

What are some honest, unfiltered things about you?

My personal mission is to change the trajectory of people’s lives who work with me. The easiest way to do this is by helping build the startup ecosystem in Metro Detroit. And the best way to help build up the ecosystem is to build a lasting organization where people can learn and grow.

Certainly, this will be measured differently for each person, though, I’m hopeful everyone will feel they have:

i. learned tremendously;
ii. reaped a financial gain;
iii. created lasting friendships; and
iv. generated tremendous satisfaction of building something special;

The tough part about this is that some people won’t realize this is happening (or happened) until much later. I’m okay with that. In fact, I’ve already received some really kind words from people who worked with us years ago (when I was doing a significantly worse job!).

I value honesty, integrity and credibility. I am terribly concerned (in life) for those who can’t help themselves (children, animals) though, I have less patience for those who squander opportunities or complain about their circumstance if they are able to make changes…

I believe everyone should follow their passions, especially in their work. The money will follow.

I have an obsessive personality. Not so much around things (alcohol, etc..) but around ideas. For example, I spent a significant chunk of years 18–25 (early 2000’s) thinking about, studying & playing poker. I’ve read dozens (if not hundreds) of books in that period. Since I was introduced to Startups (mid 2000’s) I have been obsessed with learning, building & studying them.

My word choice is intentional — both spoken & written. What I say, and how I say it is pretty measured. I was indoctrinated as part of my legal training and reinforced while spec’ing & building a software product.

I am very self aware and self-critical. Some people believe this is humility, I just think I have much to improve on.

What drives you nuts?

• Being wasteful: Wasting time, money and energy really bothers me.
• Excuses: Excuses are a dime a dozen. We all have them. There are usually millions of reasons to do things the wrong way and only one way to do it right.
• Entitlement: We’re extremely lucky to be born into a country that is free and offers opportunity for all people. We’re nearly all in the global 1%, let’s not forget that.
• Dishonesty: If you aren’t always honest, it’s unclear where you draw the line. The simplest line is choosing to be honest OR not. This alters your reliability (how often you can be counted on), credibility (how often your ‘truth’ is the real truth), and integrity (whether you value honesty and credibility).
• Passive Aggressiveness: I’ve find passive aggressiveness is a result of really poor communication and the complete avoidance of conflict. Both traits make it difficult to to work with.
• Being Cheap: Cheap is simply choosing the lowest cost option, without regard for value. Often times, the cheapest option is the most expensive. You are just deferring the costs.. [this particularly bothers me in the sales process….not with employees]

What are your quirks?

I am not scared of conflict. I love to debate. If I feel slighted or treated unfairly, I will usually call it out.

I have a chip on my shoulder. I’m not sure why, perhaps I’ve been told “no” too many times, or just been ‘bet against’ but I take it fuckin personally. It’s always personal, if people tell you it isn’t then they are lying to you.

I have a great memory. It’s not so much a quirk, except when I pretend I don’t remember things because it makes people uncomfortable how much I retained about an otherwise unremarkable moment in time.

I visualize (mentally) almost everything. Good and bad. I visualize outcomes and scenarios (before they occur) all the time. Very few things happen in a given day which I haven’t yet thought about. Because of this, I make decisions quickly — sometimes nearly instantly.

If I don’t answer immediately, my first question is almost always “what do you think?” [If you don’t have a convincing answer, I start to lose focus quickly].

How can people earn an extra gold star with you?

I have an exceptionally high bar for people — both in life, though, more importantly (for you) in a professional environment.

You should have a good understanding what it’s like to work at a fast-growing startup.

Ultimately, you’ll be measured by your track record of us working together. Until we reach that point (where we can reliably determine how well you will execute) here is a really simple starting point that requires only will power — not talent.

This list is nice, but certainly not sufficient to be successful at a fast-growing startup. Here are a few others:

• Remember that small details create BIG impacts: attention to detail can make you an indispensable employee.
• Learn (quickly) from your mistakes: (aka, mistakes are fine/expected, though they shouldn’t be repeated over and over…)
• Create solutions, don’t just point out problems: Startups are full of problems, we all know this. The key is prioritizing the most impactful issue first to keep the business moving toward its objectives.
• Consistently over deliver: Don’t wait to be handed something to do, find bottlenecks/challenges and help solve for them.

What qualities do you particularly value in people who work with you?

Excellence: I want to work with those who have a track-record of success. Most of these types of people hold themselves to an exceptionally high standard and do not accept anything less.

Leadership: Leadership is setting the tone for your colleagues to follow. Leadership is exemplified through your actions and manifest in your work, regardless if you manage people or not. The best leaders get the most out of themselves and amplify the output of others.

Commitment: I value people who go above and beyond the call of duty. I sometimes refer to this is not just being committed but showing you #outcare.

Honesty: I try to avoid people who are dishonest in all facets of life.

Integrity: See above.

Accountability: Everyone makes mistakes, though, not everyone admits their mistakes. People who pass blame onto others tend to repeat mistakes often…

Transparency: I try to be radically candid and I expect to know where you stand. I trust what you are saying is truthful.

Actions > Words: Talk is cheap. Show us you are transparent by telling us the truth. Show you are committed by going above and beyond. Show me you’re a leader by having a difficult conversation. Own it.

What are some things that people might misunderstand about you that you should clarify?

Most people probably misunderstand my value-system. They may assume I am doing what I do to be get rich (or make a lot of money). I’ve made more money both in real estate and poker (with a lot less work..)

I don’t make a lot of money. I do hope however, that I am creating a LOT of value (for myself) and others. Through 2015, my salary was in the bottom 10% of the company. I wasn’t doing this to be a hero, it was because I preferred to invest in our team instead — I figure its a smart move. For the same amount of money, I can make 5–10 employees materially better off just by paying myself considerably less than market. Today, I still make ~30% of market given our size and cash position.

They may also misunderstand my directness as being rude. I am honest, direct and deeply care about both our diplomats and the our organization. This management style could be described as “radical candor” — my style mirrors it pretty closely.

Finally, I would rather be respected than loved. I truly care about each person who works at Ambassador, it’s more important to me that they receive personal growth and achievement than myself feeling happy people like (or love) me.

How do you coach people to do their best work and develop their talents?

I push people to give their best efforts and to think analytically about their work. Often, I will ask them questions — in a socratic manner, to understand their thought process and question their assumptions.

I also have people think through a scenario, from beginning to end. Thinking through the ways a situation can play out is a great exercise in understanding how hundreds (or thousands) of pieces fit together.

Often, I’ll push people to challenge their assumptions. I do this often, regardless of the validity of their argument. It’s done to gauge their conviction (how right they think they are) and to use that level of conviction to develop a track-record for working together.

Whats the best way to communicate with you?

Clearly and directly. I appreciate clear, concise communication — especially via email or slack. I try to do the same. If I haven’t helped or you need more time with me, just ask!

If I am not “understanding” what you are trying to say, it’s likely that its just not direct enough. I prefer clear and direct statements to fluffy and vague commentary.

I prefer slack > email for questions. If you are sending me something that I need to sign (or keep) then please email it (slack makes me download it to my desktop — which is a mess!)

I am generally very fast to respond. If I take > 2 hours, it’s probably buried so you should feel free to ping me again.

Whats the best way to convince you to do something?

Show me the data then explain why it’s important to the business.

Then, explain why doing this should be prioritized over what we (you) are currently working on.

How do you like to give feedback?

In person.

Giving feedback is tough, I try to be clear and direct though, I continuously strive to get better. I just read this great article by Adam Grant on how to be better at giving feedback. (hint: it’s not by serving a feedback sandwich)

How do you like to get feedback?

Whatever way works best for you. If you prefer to slack or email me, that is fine. I’m also fine chatting in person.

PS. Want to join us on our journey? We’re hiring!