How do you transform founder habits into better operational practices?
In the early days, your operations are defined by the founder’s personal working habits. But is that the best way to work as you grow?
This week, we were excited to collaborate with Mathew Lazarus, CEO and Co-founder of Mattermore, whose mission is to transform how we work by harnessing AI and behavioral science in a personalized, private, and secure way. More from Mathew below.
No matter what we’d like to think, we emulate the actions and behaviors of our leaders, even in small and growing startups. That’s an even tougher realization if you’re the founder yourself, recognizing the weight of your subconscious on the actions of your team and the ultimate success (or not) of your startup. It’s true that 80% of our culture comes from the founder’s habits, which permeate deeply into how you do, and the operational infrastructure of what you’re building.
Your ideas matter – execution is not the only key to building a successful operation, but how you do what you do as a founder is watched by all who work with you and is ultimately mirrored and replicated to become the standard practices by which people will do their work. If you can recognize the correlation between what you’re doing and how the organization is functioning, you can then design a system that holds all working structures together without prioritizing yours in the process.
how DO you transition your personal habits into an operationally-excellent org?
Understand how a founder works, then build a system to create freedom for all working styles to progress forward.
Why This Works
Culture creates processes without rules. As soon as you have more than one person at your company, how you work becomes the implicit undercurrent of how operationally sound your org is (unless you’ve been explicit in designing this - then bravo to you!). Once you’ve set the structure from your bad habits and it permeates into “this is how we do things,” you’re choosing personal comfort over the operational performance of your team. Tiny changes can produce remarkable results. (Atomic Habits, anyone?).
Why Do This Now
There are two key reasons why it’s important to figure out how to build your operations independent from your founder’s habits.
Bad habits waste time - your startup’s most limited and precious resource. For teams without established processes, where communication from the founder is lacking or where new ideas frequently disrupt ongoing sprints, this way of working can impede progress.
Disorganized working cultures are bad for retention - unfortunately, most small companies and startups don’t have the resources (both capital and human support) required to help their team members work better. Since their day-to-day can’t be supplemented by programmed professional development, their daily learning-by-doing acts as their professional development. Creating an org where what is done is intentional and isn’t led by the whims and habits of one person, feels more supportive and cohesive.
how We Do: Figure out the itchy operations that make work difficult and invest in small changes to make them better.
According to Mathew, in the early days, there are common founder habits that, once seen and understood, can be reframed to help your team build operational structures of success.
The Habit: Toxic Empathy
This founder is incredibly empathetic, inspiring anyone who interacts with them to feel deeply seen and heard, motivating them to work with passion and dedication. This founder uses this habit to build a strong team around them. However, it’s extremely difficult to give negative feedback to someone (even in really important cases) because they’re afraid of hurt feelings. This prevents him from leveling up a team. And when you withhold how you’re actually feeling, your team can pick up on it, and it starts to create stress.
“If you care deeply about your team, be honest with them. Don’t delay their growth because you’re afraid of hurting their feelings. You’re hurting them way more by holding back”, says Mathew.
How It Affects Your Ops
Your team of “high performers” starts to experience a decline in performance. Deadlines are missed, and team members are frustrated with each other because unresolved issues are not being addressed, and there is constant modification of OKRs to align with current performance goals.
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The Habit: Extreme Vigilance
This founder is overly confident in themselves, she feels she can do anything. She uses this superpower to move mountains, especially at the beginning of the journey. But her vigilance is so extreme that she also doesn’t trust anyone else with tasks. Even if she’s delegated a task, she doesn’t give enough space for her teammate to do it their way. As the team scales, everyone finds themselves feeling micromanaged making it impossible to work with this person.
Mathew shares, “You didn’t hire amazing people to babysit them. When you trust people, they actually perform better. So trust them and get out of their way.”
How It Affects Your Ops
Things are operating slowly because there is one very clear bottleneck. If it takes three weeks to get out a piece of content, or a month to run a two-week sprint because there are daily checkpoints and revisions along the way, your speed to scale decreases dramatically.
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The Habit: Benevolent Servant
This founder has built their career on being everything to everyone. They can solve every problem. They answer every email. They always pick up when someone calls. This made them highly trustworthy in their relationships. But in a high-growth startup, when everyone needs everything all the time, this creates an extreme state of anxiety that destroys this founder’s well-being. They’re constantly burnt out and unable to take care of the most important person, themselves… which in turn makes it harder for them to show up for their teams.
Per Mathew, “Being on top of everything got you where you are, but it’s not going to get you where you want to go. As you scale, it’s physically impossible to keep tabs on every single thing. Your success hinges on your ability to prioritize and know which balls are okay to drop.”
How It Affects Your Ops
This is a meeting-heavy culture. One-on-ones on top of small team meetings on top of triple-checking and rechecking PM tools for updates which are hounded through Slacks permeate the day. Meetings are report-outs, with no room for brainstorming, deep work, or collaboration.
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The Habit: Shallow Work
This founder constantly multi-tasks. While they’re on a call, they’re sending an email. While they’re working on a project, they’re answering Slacks. In a startup when there are a million moving parts, this allows them to triage issues that come up. But it makes it impossible to do any deep work. As a result, they never achieve their actual goals for the day, and their team never feels like they’re making any real progress as a whole.
“If deep work is the key to succeeding in the 21st Century, then getting stuck in shallow work is a recipe for failure. A startup needs you as the founder to be able to step back and see the big picture. If you’re constantly putting out fires, then you won’t be able to steer the ship where it needs to go,” according to Mathew.
How It Affects Your Ops
Operations feel like a constant game of telephone. With leadership half-understanding what’s going on, teams are spending time catching each other up rather than progressing and pushing work forward.
Tools 🛠️
Tools like Mattermore or other executive coaches are an amazing resource for founders. This expert outsider can help founders see what they can’t see alone, and, while in the comfort of their own safe environment, work through the real things that are holding them back from greatness.
Take a Myers–Briggs assessment to better understand yourself as a person and a leader. Use these learnings to inform your decision-making and seek executive coaching help accordingly. Ask your team to take the assessment as well to understand personality types across your organization.
Lluna helps teams implement a data-driven approach to how team members interact and work together.
Rules (Process) 📝
The first step is to understand your core “how” habit. What is the habit that drives how you do what you do? Because how you do one thing is how you’ll do everything.
Explore how this habit is affecting the team’s operations. What’s the number one pain point of your team? Can you work backward from that effect to your habit as the cause? If you can see the correlation, it’s time to take some action to create better systems against it.
Build systems to nip habits in the bud as you work towards your own personal improvement here. Based on the habits above –
Toxic Empathy
Build clear feedback loops into your team culture.
1:1s and team meetings can have dedicated agenda items to give and receive clear feedback. It’s on the list, and it needs to be checked off. No avoiding it.
Quarterly Feedback meetings set in advance on a recurring basis help to make space during busy startup seasons to stop, reflect, and work through things that aren’t working well.
Extreme Vigilance
Often the fear of letting go comes from founders not being able to see enough of what’s going on with the team. Build a first-pass system, where all projects start with clear outlines, then have an early check-in to make sure team members are on the right track and on the same page as the founder to run with subsequent projects. That second check-in can go a long way in building trust and ultimate confidence in letting go.
Benevolent Servant
Build a decision-maker matrix to understand where you need to make decisions, and where you can rely on others to lead the charge. This is a guide, not a rule, so start here as an exercise in understanding where you can pull yourself out of the mix and let the experts do their work.
Create a clear cadence for updates, batched and reviewed collectively so you’re gaining insight without wasting time.
Shallow Work
Block out time on your calendar as “busy” for yourself. Dig into important things to ensure you take the time to guide the vision for the team.
Create clear structures of updates so you can keep abreast of key projects while not participating actively in every single meeting or collaboration session.
Consider who you’re hiring to do what. Founders who fall into any of these key habits benefit profoundly from having a generalist on their team to work on work, to build the systems and infrastructures that pull founders away from bad habits and toward operational adeptness. Having a founder proxy can expedite the process of getting where you need to be.
People 🫶
If a founder has her own habits, so does every other human working on the team. It’s impossible to design a perfect system matched with every variable behavior and habit of a growing team, but you can design a system that allows people to express their feelings and work in a way that works well for them to accomplish the team’s goals.
Take It Up A Level
Using AI to Improve how You Do:
Check out How to be a leader in an AI-powered world and As AI Makes More Decisions, the Nature of Leadership Will Change to get smart on integrating AI into your approach to leadership.
Going deeper on what you know
Leverage the tools above and carve out time to assess, reflect, and implement your leadership strategy.
Actually Actionable
Nice article. Now what?
We’ve taken the ideas above and created an action plan for you and your team.
Explore: Spend some time exploring how you act as a leader - engage with executive coaches, take a personality test, ask your team for constructive feedback, and reflect on the results.
Myers-Briggs Assessment (45 minutes)
Executive Coach Call (1 Hour)
Solicit Team Feedback (15 minutes)
Reflection (30 minutes)
Understand: Create space in your calendar to understand the feedback from your explorations and determine how to positively implement these insights into how you move forward
Two 30-minute sessions
Align: Align your team with this habit-forming strategy. Bring in speakers, utilize tools, and schedule workshops to aid in the discussions and discovery process.
Speakers and Workshops (1 Hour per Week)
Improve: Aggregate your learnings to establish structures and systems that support your team to improve your ops and how you work collectively. Build the “why” behind your how we do.
Spend time drafting your initial Mission Vision and Values (MVV) to incorporate your findings and way of working (1 Hour) (See Can you use your operations to improve company culture?)
This. stuff. is. hard. But it’s crucial to crack open what’s holding the team back and recognize the best path forward toward operational excellence. Want a high-performing team? Build a system that lives outside of the whims and working styles of a single person to ensure cohesion, collaboration, and energized ICs ready to make an impact.
Writer: Britt