Ken’s 3 Quick Tips on How to Delegate

Learning how to delegate is an essential aspect of developing your leadership skills. Without it, you may find yourself falling into a trap familiar to countless business leaders and entrepreneurs: after working long, lonely hours for months or even years, they start to see results. And, just beyond those long-anticipated results on the horizon looms something else: the ceiling. 

Eventually, leaders who fail to delegate might find themselves like the Bare King in a game of chess—they can’t win the game, yet they have to keep moving to survive. At best, they can resign the game or try to force a stalemate and end in a draw. At worst: checkmate.  

Growing, scaling, and developing a business beyond early success is a team effort. Leaders can cultivate long-term success by creating the organization, accountability, and communication structures necessary for effective and impactful delegation.  

1. Organize With Accountability

In chess, each move opens up new opportunities and vulnerabilities. Every piece, from pawn to king, commits to the same goal: win the game. They know their roles and how they can help (or harm) the mission. And, win or lose, they’re all accountable for the result.

When you organize with accountability, every team member knows 100% what they own and how it fits into the mission. Team members take responsibility for their decisions, actions, and assignments and see the impact and value their work has on organizational goals.  

For a leader to delegate to her team, she first must establish a clear structure of accountability. Without clearly defined roles and processes, employees struggle with accountability. By contrast, delegative leadership approaches flourish when there are comprehensively defined roles, responsibilities, processes, and communication frameworks. 

2. Stay in Your Lane

Leaders may need to reframe or re-examine their responsibilities before developing a culture of accountability and delegation in management roles. Instead of learning how to lead a team, delegative leaders learn how to help their teams lead themselves. 

This is not to say, of course, that the leader recuses himself from accountability. He still needs to hire the right people, train them, coach them, provide them with timely and valuable feedback, and ensure responsibilities and processes are communicated and understood. And then he has to do, perhaps, the most challenging thing of all: back off. 

As a leader, you need to coach your team members to stay in their lanes, too. After you’ve worked hard to get the right people in each role and develop them, the last thing you want is to find them taking on someone else’s responsibilities as well as their own. In other words, why send a rook to achieve in two moves what a knight can accomplish in one? 

Consistent communication and feedback from leadership empower employees to focus on their part of the board, using their strengths to help the whole team achieve its goals. 


In chess, white opens the game and gains a slight advantage. Since players don’t control whether they’ll play white or black, they develop flexible strategies to align with their goal of winning the game. They control the controllable. 

Controlling the controllable is also how impactful leaders operate, and SMART goals are an integral part of this. The SMART framework ensures both long-term and short-term strategies goal-oriented and aligns with your organization’s mission and vision. 

In an environment of accountability, SMART goals allow teams to react to changing conditions without losing sight of the target. By applying the SMART framework to task-setting, even daily to-do lists are reserved only for goal-oriented activities that are specific, measurable, attainable, relevant, and time-bound.


Learning how to delegate takes work, but the process is well worth the time and effort you put in. In my work providing business coaching services at Leader’s Cut, I work with leaders in an interactive and individualized coaching relationship to help them build stronger teams, make better decisions, and deliver consistent, impactful results in their professional and personal lives. 

If you’d like to see how executive coaching can help you achieve your professional goals or have questions about whether business coaching is right for you, let’s talk. Contact me to schedule a 15-minute coaching consultation to discover what business coaching is (and isn’t) and how it can serve you and your business.