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.

On Feedback

Company culture is a living, breathing organism you have to nurture. In a world where input and recognition are more important to today's workforce than money and title, a culture that values growth and development is well positioned to recruit and retain the best talent. Personal development starts with feedback.

The key to becoming expert at giving feedback is making it habitual and insisting on receiving it in return. You have to give feedback at every one-on-one meeting you have, whether with your manager or your direct report. 

“The key to becoming expert at giving feedback is making it habitual and insisting on receiving it in return.”

Everyone worth a damn needs their manager's support and wants insightful information about their performance. Your responsibility as a manager is to empower your team to become their best selves. When you deliver specific, constructive feedback on a regular basis to your team members, and create an environment where that same level of feedback is flowing back to you, you dramatically increase the team's likelihood of achieving superb performance.

There are significant benefits to giving two-way feedback at every one-on-one. Most crucially, you eliminate surprise. Managers and team members know where they stand, what's working, and what isn't. As a result performance reviews become a non-event, and ideally can be minimized to the lightest exercise possible. Meanwhile, performance patterns emerge quickly. Crucially, all this builds trust. Rather than awkwardly acknowledging weaknesses twice a year, the manager (and by extension the company) is constantly demonstrating that they care about personal development.

Never forget that positive feedback is absolutely necessary and should be delivered just as frequently. I need to be given thanks and told my contribution is important. The challenge is that giving positive feedback is relatively easy, and it is, unfortunately, easily forgotten. Personally, I like the discipline of trying to pair a measure of constructive criticism with legitimate praise. And vice versa. 

All great managers prioritize developing their team members, and all growth businesses need them to develop as quickly as possible. Consistently providing constructive two-way feedback develops intrinsically motivated employees that are invested in each other, and is arguably the most valuable investment of time a manager can make. Feedback can and should be the cornerstone of any world-beating company culture.

On a Management SLA

What if you published a management SLA for the whole company to use? 

Team members would have transparency into the company's management philosophy and know what kind of leadership and commitment to people is valued. New managers would know what was expected of them. They'd know upfront the gaps in their management skills that need development. The company's organizational ambition and its commitment to developing internal leadership would be clear.

Organization design's primary purpose is to provide a framework for unleashing your team's creativity. Whether you choose hierarchical, holocratic, flat, or something else, you want roles and expectations clearly understood and easily communicated. A management SLA provides a base level of consistency across all the company's teams, regardless of function, and outlines a clear set of leadership criteria that all teams can checklist against.

What might your SLA include? Perhaps frequency and content of one-on-one or performance reviews. Perhaps the need for a strategy offsite or regular team social events. Perhaps the role of team meetings or stand-ups. Whatever works for your org, if you can't write it down in a simple, digestible form that demonstrates consistency across the company, you have work to do.

When I drafted a management SLA at Squarespace and handed it off to HR to run with, the org was growing fast and new team leads were emerging just as rapidly. These team leads deserved a framework they could lean upon, and all team members needed to have a consistent experience in regards to feedback and professional development. Going forward this will help senior management evaluate team leadership across the org.

In scaling a company the most important question is what is the least amount of process and structure necessary to achieve our goals. You have to intrinsically understand the business AND the org AND the people in order to create an environment for people to do their best work. I chose the language of an SLA because it was language our engineering and customer care teams understood. By making it public, the SLA makes it safe to speak up when your manager isn't providing you the support you deserve, while also guiding the curriculum of any leadership and development programs the company is creating.

On Walking and Talking

My most productive one-on-ones don't take place in the office. They happen on the streets of Manhattan, where two miles at a brisk pace gets the blood flowing, clears the brain for creativity, and lowers defenses. On the sidewalk bullshit seems to melt away and real connections can be made. 

Walking for a meeting focuses you to get to the point quicker. Undoubtedly this is because exercise is relaxing and a change of scenery is liberating. It is far too easy for the noise of an open floor plan and the limited confines of conference rooms to start sucking the life out of you. The best part is that a walk requires you to step away from a screen and leave your phone in your pocket. 

I'm also a huge fan of the walking interview for these very same reasons. The casual and friendly nature of a walk is one of the fastest ways to get past the mutual sales mode of an interview and size someone up. 

October in New York is almost over and it's going to be chilly soon. Go take a walk while you can still enjoy it!