This is a collection of tools and behaviors for startup leaders.
Behaviors
- Say thank you
- Invest in infrastructure
- Talk to your customers every day, so they can’t talk to a competitor
- Candor
- Candor needs everyone’s participation
- Many more ideas get surfaced and improved, people learn
- Candor creates speed, faster decision making and fewer mistakes, waste
- Make public heroes of people who display it
Focus
As Steve Jobs famously said, “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are.” This is one of the hardest lessons for founders to learn. Every opportunity seems important, every feature request seems reasonable, and every market seems worth pursuing. But diffused effort leads to mediocre results.
The Power of Saying No
- Say no to features that don’t serve your core value proposition
- Say no to partnerships that don’t clearly advance your mission
- Say no to meetings that don’t have clear agendas and outcomes
- Say no to customers who want to turn your product into something else
- Say no to hiring until you’re clear on what role you need
Leverage Deadlines Deadlines force decisions and prevent endless deliberation. They create urgency that drives action and helps teams prioritize effectively. Set aggressive but achievable deadlines for key decisions and stick to them. Without deadlines, people tend to fill out the available time with things that are reasonable, but out of focus.
Communication
Effective communication is the foundation of a healthy startup culture. Here are key practices:
Email and Messaging Discipline Be careful with team-wide emails and messages. There’s a constant battle to find the right level of communication - too much and people tune out, too little and people feel uninformed. Establish clear guidelines for what warrants a company-wide or team-wide message.
Avoid Anonymous Feedback Channels Don’t use anonymous Q&A sessions or “Ask Me Anything” formats. These give a megaphone to people who just want to stir up trouble and allow negativity to spread without accountability. Instead, create a culture of open communication with:
- No retaliation policies for honest feedback
- Regular one-on-one meetings for private concerns
- Clear channels for escalating issues
- Encouragement for team members to speak up constructively
Celebrate Wins and Recognition Create dedicated channels for positive communication:
- #wins channel: Where deals, releases, press articles, and other wins are posted. Encourage everyone to contribute, no matter how small the win.
- #kudos channel: Where people can give each other recognition and appreciation. Public recognition builds morale and reinforces positive behaviors.
Avoid Acronyms and Jargon Minimize the use of acronyms and company-specific jargon. They create cognitive overhead and are hard to decipher for new team members. When acronyms are necessary, maintain a glossary and explain them when first introduced.
Leadership Tools
Clarity of Purpose, Plan, Responsibility
Make sure that every initiative has a clearly defined purpose, so people understand why it is important and how it fits into your strategy, mission, and vision.
Every initiative should come with a plan that explains the how - which steps are necessary to reach success.
Lastly, it should clearly define responsibility or who will lead and execute it.
The 5 Whys
The 5 whys is a tool for finding the root cause of a problem quickly by simply continuing to ask why something happened until you find the root cause. It originated at Toyota.
For example:
- Why did the release ship late? Because we didn’t finish all the work.
- Why did we not finish all the work? Because we thought it would take less time.
- Why did we think it would take less time? Because we underestimated the complexity of our design.
- Why did we underestimate the complexity of our design? Because we didn’t look at alternatives.
- Why did we not look at alternatives? Because we always just go with the first design.
So to solve this problem, let’s look at alternative, simpler designs before starting to build.
Decision making
Make provisional decision fast based on information available. Then define what new information would disprove it (Reid Hoffman)
You can’t steer anything until it moves.
📝 Jeff Bezos on Decision Making
Budget
Manage orgs by budget, not headcount. Your functional leaders know better how to allocate resources within their team than you do. Your job is to set the right goals and the budget. They will figure out the best way to achieve those goals within the budget.
One-on-One Meetings
Good questions to ask in a direct or skip-level 1:1:
- What patterns or trends are you seeing with your team, our department or our company?
- What would it take for us to level up our effectiveness?
- To what extent are you—or we as a department or company—reaching our potential and what is holding you or us back?
Staff Meetings
Remember the purpose of the meeting may be more for your reports then for you. While you have context on what every executive is doing, the other executives will not otherwise have clarity into their peers’ organizations. The weekly staff meetings are meant to create a forum for knowledge sharing and issue raising, relationship building, collaboration, and strategy.
Start meetings with a trip report or other personal things to foster relationships between every team member. This may feel like a waste of time when there are so many tasks to get to, but it is a good investment that will pay back in the form of a more collaborative and supportive team.
Change Management
Most internal communication failures are preventable. When a change affects a broad group of people, do not just write the announcement and hit send.
Use a rollout protocol:
- Write a clear artifact that explains what is changing, why it is changing, what success looks like, how success will be measured, and how people can give feedback. Also explain what is NOT changing.
- Vet the draft with a few trusted people who are not directly affected.
- List everyone who is directly or indirectly affected.
- Talk to the most affected people first, ideally one-on-one.
- Walk smaller groups through the plan before broad announcement.
- Announce to the full team only after the questions are predictable.
If surprising objections appear during the final announcement, you probably skipped a step.
Storytelling
Founders need to persuade customers, employees, candidates, investors, and partners. Facts are necessary, but they rarely move people by themselves.
A useful story explains:
- What changed
- What is now hard
- What reality is pushing against us
- What we believe
- What choice we are making
- What could happen if we are right
Do not hide the struggle. A story with no antagonist sounds like spin. People believe leaders who can name the hard thing clearly and still explain a credible path forward.
📝 Storytelling That Moves People
Feedback And Threat Responses
People react strongly to feedback and change because work affects status, certainty, autonomy, relatedness, and fairness.
Before a hard conversation or major change, ask:
- Status: Will this make someone feel diminished?
- Certainty: Do they know what happens next?
- Autonomy: Do they have any control?
- Relatedness: Do they still feel part of the group?
- Fairness: Can they understand why this is fair?
You cannot make every hard message feel good, but you can avoid unnecessary threat responses.
Difficult Conversations
Delayed hard conversations compound. If someone is underperforming, behaving badly, or creating confusion, waiting rarely helps them. It mostly protects you from discomfort.
Good hard conversations are:
- Specific
- Timely
- Private
- Direct
- Focused on behavior and impact
- Clear about what needs to change
- Honest about consequences
Empathy does not mean avoiding clarity. Clarity is part of treating people with respect.