Building Leadership with Loyalty, Talent and the Power of Delegation

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Since 2000, Alisa Cohn has been coaching CEOs, board members, entrepreneurs, and emerging leaders to help them increase their leadership capacity. Her specific expertise is helping leaders to think and act creatively so that they are able to step more fully into their evolving roles, scale quickly, and make the best possible decisions for their organizations. Prior to launching her coaching consultancy, she held positions at established companies like The Monitor Group and PricewaterhouseCoopers, and tech startups Corporate Alumni and Clairvergent Technology Partners.

Over the years, Cohn has developed a comprehensive process that uses a wide variety of assessment techniques (MBTI, DISC, Hogan, Firo-B, etc.) to help company leaders successfully navigate change. “I work with a lot of startups to help them build their leadership capacity,” she explains. This can be a particularly challenging task in the high-growth environment of an expansion stage company that has gone from 0 to 60 in a short period of time.

Two Key Skills of Successful CEOs

There are two key skills that CEOs need to develop and practice in order to successfully scale a company: recognizing the talent around you, and learning the art of delegation. While these may at first glance seem fairly obvious, they are among the hardest elements for Founder/CEOs to learn as they build a company from scratch. Cohn helps her clients both acknowledge the importance of cultivating these skills, as well as helping them to actually put them in action in a sustainable way.

Recognizing and Assessing Talent

Part of the challenge startup CEOs face when it comes to recognizing and accurately assessing the talent of individuals is their close proximity to the team. “Early-stage startup CEOs are in the trenches with their employees and certainly with their executive teams,” Cohn says. “When you’re building a startup, you’re working side-by-side, eating cold pizza at two in the morning, and giving all your blood, sweat, and tears.” This level of intimacy is necessary in the beginning, but it can give otherwise savvy CEOs a blind spot.

“Because of how closely they work with their teams, new CEOs have an incredible amount of loyalty to their people,” Cohn explains. “This is a wonderful quality, but it may not allow the CEO to accurately assess each person’s talents, strengths, and weaknesses.” It’s a little bit like the old adage about being unable to see the forest for the trees. In addition, startup CEOs also have to factor in that the organization is in a constant state of change and, as a result, the kinds of people needed for different roles is also in a constant state of change.

“Some people are really well-suited to helping early-stage startups get off the ground. But that doesn’t mean that those same people will transition well into leadership roles in a larger organization in which you have to coordinate across different groups of people, product lines, and so forth.”

Cohn advises CEOs to learn how to look at their teams objectively. “CEOs need to be able to consistently look at their team analytically,” she says. “They need to figure out which individual is the right fit for each role in the existing organization, not the organization of a year or six months ago.” Only when the CEO can maintain this perspective will he or she be able to make the right decisions about who to put in key roles as the company grows.

Delegating Power and Responsibility

On a related note, delegating is a critical skill for CEOs whose roles are evolving in a growing company. While it can be difficult to extricate themselves from the day-to-day operations of the business, they must do so if they hope to ever step fully into the leadership role that is their ultimate responsibility.

“At a certain point, the CEO can no longer control everything or even have a say in every decision,” says Cohn. “Instead, they need to have hired or otherwise identified the right people and put them into the right roles. Then, they need to share their big-picture vision with this group and get out of the way.” Cohn often sees CEOs who fall into the trap of believing that they are only adding value if they are doing something.

“Sometimes adding value is choosing to step back and do nothing. Sometimes, and this is true for executives as well as CEOs, the most valuable thing a leader can do is say, ‘I have great faith in you. I have every confidence that you’ll be able to do this.’ and then let them figure it out.”

In this way, delegating is more about empowering people to work independently than it is about getting tasks off your plate.

Cohn also points out that CEOs who are doing a good job of staying out of the day-to-day operations will not have the right line of sight to make the best decisions in those matters. Once they have removed themselves from the trenches, they must realize that the decisions at this level are best left to the people who are immersed in the issues on a daily basis. “When the company gets bigger and starts moving faster, those are the signals that the CEO and other high-level executives might, at times, be in the way,” she says.

Signs that It’s Time to Transition Out of the Trenches

Even CEOs who grasp the concepts of properly assessing their team’s talent and delegating responsibility accordingly can have a tough time knowing when it’s time to, as they say, cut the apron strings. What are the key indicators that it’s time for a startup CEO to transition from doing to leading? The answer to this question is slightly different depending on the business model, industry, and individual company, but there are a couple telltale signs that Cohn has found to be pretty consistent markers: size and speed.

“The first and easiest sign has to do simply with size,” Cohn says. “When the team is getting bigger, the number of direct reports is getting unwieldy (typically seven or more), and the CEO no longer knows exactly what everyone is doing, it’s time to think about making a transition.”

The other milestone that is a clear indicator that it’s time for the CEO’s role to evolve is when the company has established a clear product-market fit and anticipates a period of rapid growth. “When you’ve demonstrated product-market fit and are ready to scale, you have to be really sure that you’re operating in a mode that’s built around processes and systems, not command and control,” Cohn says. “You have to trust the structures and people around you so that you can step away and focus on managing high-speed growth, knowing that your team will step up to a new level of responsibility .”

Cohn is quick to clarify that you shouldn’t wait until the last minute to start assessing talent and delegating responsibilities. “You should already be headed down that path by the time you reach this point in your company’s growth,” she says. “It’s just that, at this stage, change becomes compulsory.”

The Core Concept: Empowerment

When all is said and done, Cohn’s work converges on a single concept: empowerment. In her work, she helps empower CEOs and other leaders; and much of what she teaches them is about empowering others. “It’s so important for CEOs to learn how to hire the right people, delegate power to them, and hold them accountable in a way that helps them grow professionally,” she says. “It’s not about keeping a scorecard with wins and losses. It’s about being a force for good, a force of encouragement, calm, and even-keeled leadership.”