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Running a company as it begins to grow is a bit like navigating L.A. traffic. Sometimes, a roadblock ahead creates a bottleneck, slowing everyone’s movement to a crawl.
As a leader, it’s humbling to realize that at some point — after pulling 16-hour days, 7 days a week, for years to launch a business — you have become your organization’s bottleneck, holding up progress. But that moment is inevitable in a company’s evolution. The hardest part? Accepting the reality of your changing role and learning to delegate.
I’ve been at the helm of an organization from its earliest stages through its expansion into a parent company of that brand and many others. That leadership ascension has given me insight into the continual process of letting go and empowering your team to do their best work so you can continue to grow the business together.
It begins with an internal reckoning
Decision fatigue, stagnating execution, your team’s dependence on you for constant approvals — these are signs that the type of hustle that brought you to a certain place won’t carry you to the next. It’s time to transition from task manager to team leader.
But stepping back from everyday operations and lower-risk decision-making requires an ego check. In my roadblock moment, a mentor encouraged me to look around and recognize that there were people on my team who could perform some tasks better than I could. He was right. Surely, someone with a design background should choose the color of the marketing materials. Why was I still holding up that show?
Moreover, when I set my ego aside, it became clear that the team collectively added dimension to the innovation process that no individual could, no matter how well I knew the business.
Making the cognitive leap from doing to leading is challenging. Early on, you measure your success by how many tasks you accomplish. However, as you move toward higher-level leadership, you have to measure success by your ability to take a group of people from one place to another. Executive coaching and mentorship can help recalibrate your personal metrics of success to align with your evolving role.
Related: As Your Company Grows, You Need to Stop Constantly Dealing With Day-to-Day Fires
Building trust and systems
Getting out of your own way is only the first step. Learning to delegate also requires assembling a team whom you can trust — and who can trust you.
Building professional trust is an ongoing process, just like in personal relationships. In business, it means establishing a common understanding of judgment, approach, behavior and diligence—things that demonstrate that even if the outcome is not always perfect, the process to get there was thoughtfully conceived and implemented.
Engendering trust within an organization goes both ways, too; employees need to feel empowered to make decisions. Bottlenecks persist when employees seek unnecessary approvals because they don’t believe leadership will respect their judgment or they’re afraid a mistake will cost them their job.
At my company, we intentionally work to create a culture of psychological safety to ensure employees feel confident to take on greater risks and responsibilities. We make it known that dissenting opinions are encouraged and teach our teams to healthily manage conflict through actively listening and respectfully responding to all ideas. Following our own version of a “courageous conversations” initiative, we’ve seen an uptick in these types of meaningful conversations in now-shared vernacular throughout the organization.
Alignment around values and purpose is also crucial to building mutual trust. We formalize behaviors—like welcoming a diversity of opinions—by baking them directly into our company values statements.
Since our company’s earliest days, we’ve cultivated these mutual values through a range of leadership development programs, some of which I’ve personally taught. The idea is to get everybody on the same page regarding company strategy and goals, as well as processes for sound decision-making. Each program also addresses the skill and importance of delegation. We’ve seen a waterfall effect occur as managers take these learnings and context back to their teams, and teams put them into practice.
Related: 5 Tips to Master the Delicate Art of Delegation
Knowing when to zoom back in
Delegation often requires zooming out as your company grows. But sometimes, you need to zoom back in.
Identifying critical moments to reengage is a perennial challenge. Patience is key here. But it’s difficult without any information about the problem. When I see bulging budgets, ballooning timelines or teams failing to interface productively, my ears perk up, and I start to dig before deciding whether to dive in.
If a situation does seem to need my intervention — or my attention may solve it faster than our regular channels could — my goal is to toe-dip rather than take a long swim. I meet with key stakeholders to better understand the expressed and sometimes unexpressed issues, as well as whether discussions and alignment are progressing. We agree on the facts, problems and goals, then push to resolution. This helps me get in and out quickly to enable normal processes to resume. Being continually pulled back into a situation is a red flag that processes or leadership may need a tuneup.
Related: How to Effectively Delegate at Work and at Home
Flexing your delegation muscle
The ability to delegate isn’t binary — it’s not something you can or can’t do. It’s a practice you develop over time, and you must continually adjust to new circumstances as they arise.
If the idea of letting go, even a little, feels overwhelming, start by relinquishing low-risk decisions. For example, begin with choices that affect the company internally rather than those that directly impact clients. Put others in charge of things like setting internal meeting agendas and drafting internal memos. As you establish mutual trust — you see that your employees make solid decisions without your input, and they see that you respect their judgment — you can begin to turn over higher-stakes issues.
Ultimately, true leadership is about getting people to understand that you’re all working to solve the same problems and building systems that empower them to thrive independently while working toward these shared goals. By enabling your team to confidently unleash their brainpower to innovate and push the company forward, everybody wins.
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