Humility and Fierce Resolve

I pulled out my notes on Good to Great to find a quote or two for yesterday's blog post on self-awareness. Inevitably I found other quotes meaningful to me. They speak for themselves and since my drafts queue is full of half-finished ideas, allow me to simply share them with you below. You'll find my brief comments in italics. The title of this post refers to the two key qualities found in all of Collins' Level 5 leaders.

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Management and leadership is not about those doing the managing and leading, but rather about those being managed and led.

... Level 5 leaders have ambition not for themselves but for their companies ... Level 5 leaders want to see their companies become even more successful in the next generation and are comfortable with the idea that most people won’t even know that the roots of that success trace back to them. As one Level 5 CEO said, “I want to look from my porch, see the company as one of the great companies in the world someday, and be able to say, ‘I used to work there.’ ” 

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The hardest thing a manager has to do is let someone go. It is always gut-wrenching for both parties. To be great you must relentlessly focus on the long-term ambitions of the company. As a result tough decisions become necessary and obvious.

Letting the wrong people hang around is unfair to all the right people, as they inevitably find themselves compensating for the inadequacies of the wrong people. Worse, it can drive away the best people. Strong performers are intrinsically motivated by performance, and when they see their efforts impeded by carrying extra weight, they eventually become frustrated.

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When it comes to product, Squarespace's Anthony Casalena embodies this lesson more than any founder I know.

Good is the enemy of great. And that is one of the key reasons why we have so little that becomes great. We don't have great schools, principally because we have good schools. We don't have great government, principally because we have good government. Few people attain great lives, in large part because it is just so easy to settle for a good life.

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Only rocket science is rocket science and only saving lives is saving lives. The rest of us should remember that work is just work. Don't overthink it. Focus on your family and choose work that is deeply meaningful to you. The rest will follow. For me that means choosing to help grow teams creating innovative software that has tangible and meaningful impact on the lives of the individuals who use it. 

When [what you are deeply passionate about, what you can be best in the world at and what drives your economic engine] come together, not only does your work move toward greatness, but so does your life. For, in the end, it is impossible to have a great life unless it is a meaningful life. And it is very difficult to have a meaningful life without meaningful work. Perhaps, then, you might gain that rare tranquility that comes from knowing that you’ve had a hand in creating something of intrinsic excellence that makes a contribution. Indeed, you might even gain that deepest of all satisfactions: knowing that your short time here on this earth has been well spent, and that it mattered.

On Self-Awareness

“What is your damage, Heather?”

— Veronica Sawyer

Those of a certain age <ahem> will remember this comeback from the halls of high school. The question, however, is critical. Those who achieve self-awareness likely have spent a significant portion of their lives exploring the answer.

Jim Collins discusses the role of self-awareness in leadership in his seminal book Good to Great. “Level 5 leaders [Collins' highest order] are a study in duality: modest and willful, shy and fearless.” Leaders able to project conviction yet be truly and constantly receptive to dissent and ideas from throughout the organization cannot exist without high degrees of self-awareness. 

“Without knowing your damage, you may be capable of determining what makes you tick but you will be blind to what makes you react.”

Self-awareness is my number one predictor of future success because it essentially predetermines one’s capacity for growth. Combine self-awareness with exceedingly high levels of intellect and curiosity and – BOOM – you’ve got a winner on your hands. Add experience and the necessary winning personality to the mix and you should do all you can to prevent the candidate from walking out the door. But please don't break the law like Veronica and J.D. did.

Without knowing your damage, you may be capable of determining what makes you tick but you will be blind to what makes you react. If you’ve often found yourself angry, defensive, or aggressive, there is a deep seated fear that is being triggered. Walling it off may have saved you as a child but it’s limiting you as an adult. The truthful exploration of your joys and traumas, your desires and needs, and your habits and peccadillos is necessary to understand why you do the things you do. 

Collins posits that great companies "became relentlessly disciplined at confronting the most brutal facts of their current reality." I say this is true of great leaders as well. I devote considerable energy to this exploration. The mind doesn’t want to walk down these unpleasant avenues. The psyche is built to defend itself. Reflecting on your shortcomings is a choice you must make. How can you improve a habit if you don’t understand its origins? You empower yourself to internalize life’s lessons and achieve new levels of personal and professional success if you can closely and critically observe yourself, particularly when you are exposing the raw wounds of the damage holding you back. 

Too much unexplored damage and, one way or another, your behavior will change to the point where it's noticeable to others. If you aren’t self-aware, it means your mood is being affected by something you don’t know (or want to know) is bothering you. If you are self-aware however, you are constantly practicing being your best self and rising to the occasion. If one is conscious as to who they are, how they think, and what they fear, they have the tools to affect their own change. Self improvement is impossible without self awareness. 

“The mind doesn’t want to walk down these unpleasant avenues. The psyche is built to defend itself. Reflecting on your shortcomings is a choice you must make. ”

Self-aware teams persevere through adversity and learn at ever increasing rates. Self-aware managers know how to build effective teams because they challenge their teams to become ever more aware of what motivates and stifles them (collectively and as individuals) and thus their decision making. A highly functioning team knows who each team member truly is, how they think, and how the combos of those thinking modes interact. Highly functioning teams have the courage to own their behavior and they use this collective self-awareness to be the change they wish for. Smart, curious, self-aware teams can achieve any goal and carry out any plan.

I've previously written about wanting to build heterogeneous teams of people who are continuously exploring their gifts and their shortcomings and building each other up as a result of those explorations. How do you identify these candidates? Brains and experience and niceness can all be tested. Here are just a few of the questions I mix into a 60-90 minute conversation that I believe expose a candidate's level of and capacity for self-awareness:

• What's the single most important thing you do every day?
• Describe a time you felt you were right but you still had to follow someone else's directions.
• What were you doing the last time you looked at a clock and realized you had lost all track of time?
• What business do you fantasize starting?
• What would you most like to learn working at MyCo that will help you in your future after MyCo?
• Where do you not want to be in five years?
• What would you say is the biggest misperception people have of you?
• Without thinking quickly name three reasons why I should not hire you.
• Tell me about the last time a co-worker or customer got angry with you. What happened?
• What do you enjoy most about working and what do you enjoy least?
• Are you nice? When are you not nice? Tell me about the last time you were not nice.

Self-reflection can take place anywhere at any time. I’m getting better at the habit of writing a few things down when I’m feeling agitated and reacting emotionally. It’s difficult, and the answer isn’t always there. But growth starts with asking ‘Why?’. If I can learn to spend more time seeking to understand rather than to be right, I’ll end up understanding and being right more often.

Ten Rules

1. Focus unswervingly on the customer.
2. Make and beat audacious goals.
3. Hire the best and brightest, without equivocation, and exceed their expectations by over-delivering on what motivates them.
4. Invest continuously in learning, mentoring, and development.
5. Help the people around you excel, and in turn excel because of the help of the people around you.
6. Trust in the abilities of one's colleagues.
7. Reward and emphasize personal accountability.
8. Rip off band-aids quickly and cut loose dead wood.
9. Act with urgency.
10. Be human.

(Number 11 would be don't mix metaphors like I did in number 8.)

On Candor

Build a culture centered around speaking the truth, and you create an environment that nourishes courage, encourages risk taking, and regularly pushes your business through new thresholds.

Look into the companies you admire and you'll notice candor sits at the core of the culture of these great organizations. Without it, ideas are squashed before they see the light of day, while those ideas that do surface don't face hard questions from day one. Candor is also the one problem solving technique that works in any situation. 

“Candor is the one problem solving technique that works in any situation. ”

As a COO I am constantly collecting information across the organization, strengthening the decision making ability of the executive team and gathering the data I need to build and iterate the systems, processes, and organizational structures necessary to support rapid growth. By bringing what is seen and thought throughout the org into the light, decision makers are best informed as to the risks and opportunities they face.

As a leader my responsibility is to tell hard truths to my team and to my CEO. I can only do that when folks truly believe that I have their best interests at heart and my intention is to push them to being their better selves. 

Below follow some of the principles for candor I have imparted to my teams, principles I do my best to follow in order to create high-performing environments built on reservoirs of trust.

Pursue Self-Awareness

A culture of candor can only exist when the example is set from the top. There can be no space between what we say we value and what is actually demonstrated. It therefore necessarily starts with my being self-aware and confident enough to discuss what I'm good at and bad at. That builds trust. It continues with openly assessing how my decisions and choices pan out, and sharing the lessons I'm learning along the way. If I can't manage myself, how I can manage others?

Self-awareness is my number one test in interviews. I want to build a team of people who are continuously exploring their gifts and their shortcomings. Since the best teams are heterogeneous, candidates who know their strengths and weaknesses help me build a team of diverse skill-sets and life experiences. These same people understand what motivates their decision-making. As in everything hiring related, you must identify what you want your company to be and then hire the folks with the DNA to make it so.

Admit What You Don't Know

I have one cardinal rule: If you don't know, say so. There is no crime in missing a deadline, screwing up, or being wrong on an educated assumption. The only sin is not admitting what you don't know and trying to fudge your way through it. Unknowns and uncertainty are everyday facts at a high-growth company. You will never be penalized for not having learned something yet. 

Be Vulnerable

To learn from your mistakes they must be put on the table to be discussed in the light of day. Vulnerable leaders who repeatedly demonstrate an ability to candidly assess and discuss their own weaknesses and failures build powerful bonds with the teams they lead. Similarly, vulnerability builds trust between teammates, and trust ensures strong, long-lasting relationships characterized by the strength to persevere through the inevitable roller coaster that is startup life.

It's not a weakness to show weakness. The fear of failure gets in the way of creativity. Once you accept perfection is an impossibility and that you don't need it to be successful, you will start risking more to achieve more. You'll discover step functions in your performance and results, proving yourself infinitely more valuable than conservative Joe Perfect ever could be. 

Create a Safe Environment

I want – no need – truth spoken to power. Sometimes it hurts and sometimes it takes time to process. But it's never not worth it. When tough news is delivered plainly the problem gets addressed faster and we can all get back to building and doing what we do best. As a leader, set the example. When your teammates take the same risk, reward them.

A safe, candid environment brings more ideas into meaningful conversations. The key skills needed to create a safe environment for your team are (1) to listen, without judging or feeling judged, (2) to be critical, without being judgmental, (3) to propose solutions, rather than simply criticize, and (4) to disagree, without making the other party defensive. Without these your candid culture will devolve into an intolerably competitive one. 

Be Nice

Candor can be the most powerful instrument in your toolbox, but don't be a jerk. Blunt isn't the same as candid, and you have to have a strong EQ radar to deliver the right message in the right way to each person you interact with. Otherwise the message gets lost due to the messenger. Being candid is about being open with your cares and concerns, and giving advice with pure intentions. We are actually showing respect when we assume someone has the strength to hear the truth and the character to learn from it. 

Tell a Story

You can't deliver all of the news to all of the team all of the time. Sometimes taking the time to craft a story with meaning from your raw data or feedback is essential to getting your message across. Everything in life starts with communication. Be sure to get the right information to the right people at the right time in a manner they can digest. 

Have Courage

We all desire to surround ourselves with exceptionally smart and curious people driven to succeed and unafraid of obstacles. That's the primary appeal of startups for me. Let your team know that blowing smoke up your bum isn't what you need to be the best leader, and certainly isn't the key to their achieving their goals and ambitions. 

Invest in the work necessary to build a candid culture by setting an example every day at the top and rewarding model behavior at all levels of the org. Reinforce that the courage necessary to speak one's mind is strength you want to invest in. You will unlock ideas and your talent will have the best chance of reaching their potential.

On Recruiting, Part One

We can be sure we are building a successful recruitment strategy and brand when a candidate we reject refers a candidate we hire. 

My recruiters and team members have heard me preach variations of this theme for years. I usually get a strange look the first time they hear me say it. My point is simple: if we spend our time focusing on details and dignity in the candidate experience, the payoff for all parties will be substantial. And when a recruiter closes their first successful rejected candidate referral, the lightbulb goes off and the purpose of all the work we put into recruiting becomes clear.

“Every candidate who applies to your company isn’t just a prospective employee. They’re a prospective customer.”

Recruiting is about relationships. Every candidate who applies to your company isn't just a prospective employee. They're a prospective customer. Evangelist. Source of talent. 

And never, ever judge a book by its cover.

The basic premise is simple: treat everyone awesome. You don't know who the A+ player is before she walks in the door. And you don't know who the B- player is friends with when they walk out the door. Every candidate that works their way through your recruitment process will undoubtedly share their impressions and experiences with their friends. This will impact your brand.

Be sure to keep in mind these important facts: engineers know other engineers, designers know other designers, product managers know other product managers, and marketers know other marketers. Duh.

Details matter:

• Where do you place the job ad? What does it look like? What does it say? Did you ask why in answering all three questions?
• Sweat the structure and copy of the job description. What do you mean to say? What values must be transmitted? How are you representing your culture? What are you choosing to leave out and why (I often make choices here to test for what questions candidates ask)? Are you flighting multiple JDs for the same position to attract different applicant pools?
• How have you designed your interview welcome experience before candidates arrive? What does the candidate receive beforehand to set their expectations and put them at ease? Do they have a single point of contact who is regularly in touch, particularly the day before the interview?
• How have you designed your interview welcome experience once they arrive at your office? Where are they seated to wait? Do you want them to see the buzz of the office or have privacy to collect their thoughts? Have you provided a WiFi password, an iPad to pass the time, or some reading material on the company? 
• Does the day start with a member of the recruiting team taking them to the interview room and reviewing the day's agenda, offering to answer any questions, and generally putting the candidate at ease? Did you offer them a drink and show them where the restrooms are?  Is food or lunch on the agenda? Are they in a glass box where everyone can walk by and stare at them or do they have some privacy?
• Do interviewers introduce themselves, explain their role in the company, and set out their goals for the interview and agenda for the hour? Do they look candidates in the eye and shake hands like a grown up? Do they leave their phones back on their desk? Leave enough time for questions? Provide a card or email address for follow up questions (and to make it easy for the candidate to send a thank you note)? Are candidates offered a rest and a drink before the next interviewer enters the room?
• Does the day end with the same member of the recruiting team debriefing the candidate? Providing a sales pitch? Collecting feedback on the process and on the individual interviewers? Does the recruiter make notes of new or unanswered questions?
• Within 24 hours has the recruiter followed up with answers to those questions? Is the candidate thanked for their time by the company? Have you asked the candidate how we did (perhaps with a short feedback survey)? Solicited them for further questions?
• Within 72 hours is the candidate's standing in the process clearly communicated? Are next steps delivered in a timely manner? Are expectations properly set.
• Etc.

Dignity matters:

• Are you respecting the candidate's time and other commitments?
• Are you answering their questions honestly, transparently, and in a timely manner?
• Is the entire process timely? Does it feature regular and excellent communication?
• Are rejections delivered humanely and verbally by the recruiter or hiring manager who knows the candidate best and shepherded them thru the interview process? Did you acknowledge their strengths? Did you thank them for their time?
• Are candidates offered an opportunity to receive feedback on their interview process so they too can learn and take steps towards being their best self and achieving their career goals? 
• Etc.

It is deeply satisfying in building a company to deliver an awesome candidate experience to someone, unfortunately having to reject them but doing so with compassion and dignity, and having them in turn recommend your company to someone they feel would be a better fit than they were. When candidate pools are tight and markets are competitive, every detail counts.