My first startup failed, and I realized the reason it failed was that I was an ineffective leader.
When I returned to college, I took every opportunity to learn how to lead well.
I became pledge class president of my professional fraternity my junior year. My senior year, I served as VP of Marketing and ran the highest attending rush week in fraternity history.
As a design student, I started the main UX design organization at UC Davis. In our first quarter, we received over 60 applications to join as a designer. We ran projects with real clients, everything from startups to Grubhub.
These are the principles I’ve learned and written down that made me a better leader.
Trust and consistency
Trust makes for a strong org, and consistency builds trust.
When I was working on my startup, I was not very consistent. If your team can’t depend on what you say, then they can’t depend on you at all.
After shutting down my startup, I encountered Stephen Covey’s classic, Speed of Trust, which arrived at this exact conclusion. Organizations that have high trust get things done a lot faster.
When I led DI (Design Interactive), the student-run design agency at UC Davis, one reminder I kept on my wall was: “Engender trust every day.”
At every meeting I led, every project I directed, every 1:1 I had, I thought about whether the way I showed up engendered or eroded trust.
Test everything
This seems obvious nowadays, but we really tested everything.
For example, when it came to branding, we tested several names and visual identities to see which one students recognize most easily as a UX design org that works with real clients and which one they would attend an event for. Design Interactive was not our first choice name, but it was most direct in communicating what we were about. Our original visual identity was far too sophisticated, and seemed offputting to students, so we chose something much more friendly and approachable.
For events, we included surveys on how students heard about it so we could learn about our marketing effectiveness. We looked at the conversion rates from public events to member applications to see whether we were maintaining both reach and selectivity quarter-to-quarter. We looked at whether designers stayed on after their cohort to apply for leadership roles or to mentor others to ensure we were building a culture of giving back.
Decision rights
This one I learned at my first product design internship at Alation when one of our investors, Gokul Rajaram, came in to give a fireside chat.
His phrase “decision rights” was an instant unlock. I realized so many disagreements and conflicts in teams came because no one knew who actually had the decision right.
If you ever see decisions go back and forth endlessly in a meeting (between product and marketing, for example, or between a designer and PM), or where a decision just doesn’t get made despite repeated meetings, observe whether there is a clear sense of decision rights.
Often times, there’s not.
Situational leadership
This came from one of my favorite business books, Leadership and the One Minute Manager: A Situational Approach to Leading Others, by Ken Blanchard.
The basic insight is that there’s not a single right leadership style for every report and for every situation.
Instead, you should diagnose where the report is in their competency for the task.
Are they:
D1: an enthusiastic beginner (low competence / high commitment)
D2: a disillusioned learner (low to some competence / low commitment)
D3: capable but cautious (moderate to high competence / variable commitment)
D4: or a self-reliant achiever (high competence / high commitment)
Again, this differs not just by person but also by what they’re doing.
Then you have various leadership styles:
Style 1: Directing (high directive + low supportive behavior)
Leader provides specific directions and closely monitors performance to give feedback.
In directing, you tell the person what the goal is and what a good job looks like, you give them a step-by-step plan about how to accomplish the task, you solve the problem and make most of the decisions, providing feedback and relying on the person's willingness to learn and transferable skills.
Style 2: Coaching (high directive + high supportive behavior)
Leader continues to direct task accomplishment but also encourages involvement in decision-making.
In coaching, you begin to engage in two-way communication, though the leader still makes the final decision.
Style 3: Supporting (low directive + high supportive behavior)
Leader and individual make decisions together; the leader's role is to facilitate, listen, draw out, and encourage.
In supporting, you would rarely talk about how a person should solve a particular problem but you ask questions that expand their thinking and help them build confidence by finding their own solutions.
Style 4: Delegating (low directive + low supportive behavior)
Individual makes most of the decisions and gets support from themselves or colleagues; the leader's role is to value the individual's contributions.
In directing, you are handing over responsibility of day-to-day decision-making.
Your goal as a leader is to gradually increase the competence and confidence of your people so you can begin to transition to less time-consuming managing styles.
I used this framework leading DI.
For example, one person I worked with was naturally a strong communicator and very confidence-inspiring, so I gave her the account manager role for our biggest client. I saw her as D3 in this matter, capable but cautious, so I took a supporting leadership style. Frankly she had more talent at client relations than me, but since she had never done the role before, I wanted to be there in a supportive role to have her back if she needed more resources or a pep talk. She played a fantastic role in achieving the desired results for that client.
For another person who was leading marketing for the agency, she proposed some social media campaigns. I thought she was a D2 in this, a disillusioned learner, so I worked with her closely in a coaching leadership style to both show her the ropes and let her make some of the decisions.
Situational leadership is an expanded form of servant leadership, so a good thing to reflect on is whether the people you manage would say you were serving them well.
Culture is a pattern of behavior that’s rewarded and punished
Ever since I heard this, I’ve noticed how true it is at every org I’ve been part of.
Putting this into practice at DI, I would subtly reward people who were unusually open about sharing non-consensus ideas in meetings, or for people who paid special attention to the welfare of their design team or clients. The rewards were informal, for example, a shout out at a meeting, or a private word of praise. But this worked to grow the culture toward excellence and non-groupthink.
We also started large weekly meetings with the one-breath ritual, which fostered a culture of authenticity and genuineness.
Punishments were also doled out. Most of it was also informal. For example, I believed strongly in starting meetings on time, because it is everyone’s time that is lost waiting for those who are late. At DI, I set the norm of always starting meetings exactly at the scheduled time with no delay. Over time, people learned that if you are late, you miss out on information.
Be personal
I truly cared for every one of my reports. Whether it’s their job search, their schoolwork, or their projects with DI, I was there for them.
I believe leading with empathy and candor was what made our team so committed.
This was balanced by letting my reports set their own weekly goals, and me enforcing them.
My team knew I cared about them, but they also knew I would be on their ass if they fell short of what they said they would accomplish.
Let people fail
When I ran my first startup, I didn’t trust people enough to delegate. And it was my biggest mistake.
When I ran DI, sometimes a report would suggest an idea that I was pretty sure wouldn’t work. However, if they were new to it, I would allow them to try it out and see the results for themselves rather than correcting them before they’ve been given the chance. Over the long term, I believe this fosters more boldness and ownership.
It’s the opposite of micromanaging.
I really believe in this because I’ve been on the opposite end, where someone who was my superior would not give me any freedom and would tell me exactly how they wanted me to do everything. It was as if I had to be a clone of them and make every decision exactly the same way. It built resentment and meant that I couldn’t learn from my mistakes.
When the best leaders' work is done, the people say, "We did it ourselves."