On Candor

Jesse Hertzberg
4 min readDec 9, 2014

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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.

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.

Originally published at www.titleneeded.com.

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Jesse Hertzberg

CEO @Livestream. Helped build @Squarespace, @Etsy, and @BigSoccer. Trying to keep up with operations at home. My opinions are my own.