When you see an employee struggling with a task you can easily do, it’s natural to want to step in and help. But from the other side, it can feel more like micromanagement than support. And when leaders over-function by keeping too much work for themselves, they allow those around them to underperform. We all know how important delegation is — both to help employees grow and to create a more collaborative, empowered, productive team. How can you get better at this key leadership skill? First, shift from a do to a leader mindset. Second, embrace the discomfort of the learning process. Third, identify low-stakes tasks that are less risky to delegate. Finally, be curious and facilitative rather than prescriptive.
“How do you justify the sales and cost estimates?” asked the CEO. My face was red from stuttering. My chest tightened and my throat tightened. I looked at my boss, Valerie. He made eye contact, looked slowly, and said nothing.
He could have eased the heat of my path by speaking and saving me, but he didn’t. That’s because I asked Valerie for an opportunity to present to our organization’s leadership team. Before the meeting, he informed the head of our banking division and the CEO that I will do this work and that he will be an observer. So, instead of taking my place when I faced difficult questions, he let me get out of my trouble. I messed around with it, though not as well as I would have liked, but somehow more prepared for my next meeting with him.
I remember Valerie as a good boss because she always gave me opportunities to grow like this. The stakes are usually as low as that small, internal meeting, where everyone knows I’m still green and supportive. Valerie is there but in the background, allowing me to succeed or stumble but learn from the experience either way. Afterwards, he stopped giving me a long list of suggestions on how to improve. Instead, he asked great questions that prompted me to think about what I could have done differently.
In theory, most leaders know how important it is to delegate challenging tasks to employees to help them grow and create a collaborative, empowered, productive team. But, faced with the real needs of the workplace, it can be difficult to implement it. Many of my clients say things like “I can only do the work” or “If this project doesn’t go smoothly, the whole team will suffer.”
Empathy is possible A barrier, too. When you see an employee struggling, it’s natural to want to step in and help. But from the other side, it can feel more like micromanagement than support. And when leaders over-function by multitasking, they allow their teams to become dysfunctional.
Here are some strategies you can use to make delegation easier.
Shift from do to think leader
At my corporate job, we promote top performing leaders. It came with an assumption that they would magically move from being good and motivated by performance excellence and rewards to excellence and caring deeply about developing the potential of others. The mindset shift can be the hardest part of all. So, how can you make it easier for yourself?
- Note your wages from ACT. The excitement of success gives a quick hit with dopamine. But that’s something you have to resist in order to get the greatest fulfillment in helping others thrive.
- Claim your leadership by clarifying values. Ask yourself: What three words would I like people to use to describe my leadership style? Example: Do I want to lead with control, urgency, and skill? Or, with patience, curiosity, and empowerment?
- Intend to respond, not react. In moments when you are prompted to join, ask yourself: Does that match my values and who do I want to be as a leader?
Embrace the discomfort of the learning process
Many leaders have told me that, after witnessing an employee burn out, taking the job back seems like the most supportive thing to do. I feel this tension too. But Valerie taught me the power of holding space for struggle. Yes, it creates discomfort for the leader and employee because it is a new way of working for everyone. But, as Gallup reminds us, one of the keys to engagement at work is the opportunity for motivating challenges. And if you push the struggle, the result is growth for all parties.
How can you embrace, rather than resist, the discomfort of learning?
- Name your emotions, that according to Psychologist Susan David, offers clarity and strength and can empower you to respond in an intentional way, aligned with your values.
- Normalize discomfort. Neuroscientists know that these are the times where learning takes place and perseverance is developed.
- Reframe the situation. A potential reframing is: “It allowed me to struggle and where I gained confidence in my skills. So I give my employees the same gift of time to solve the problem themselves.
Distinguish between high and low stake tasks
Leaders often tell me that they remain stuck as doers because employees make too many mistakes that have an impact that requires intervention. But it usually happens when the bosses themselves hold all the work for a long time and then are forced to delegate at the wrong moment. The key is to assign assignments when the stakes are low and missteps are allowed, or even expected.
What makes a low-stakes environment? Failure supports learning more than damaging reputation. Mistakes do not affect the success of the team or company. The environment is safe for stops and do-overs. The people involved have support and compassion for less experienced colleagues in learning curves.
To determine which tasks are ripe for delegating, think about the ones you currently feel are easy or remember you but are good development opportunities for your colleagues? Also consider a job that drains your energy and doesn’t match your skills, talents, and strengths but can be exciting and feel worthwhile to others.
For example, if your employee’s goal is to develop better presentation skills, try a low-stakes activity like asking them to lead the next staff meeting before a high-stakes one. such as conducting a client meeting. Or, if they want to get better at influencing others, challenge them to get buy-in from a small team in using a new tool or work process before asking them to persuade your whole which division to implement it.
Be curious and quick
Early in my corporate career as a trainer, people told me that I was visibly nervous in the sessions I led. I explained to my boss that I was worried that there were no answers to the participants’ questions. His response: “What if your role wasn’t to have all the answers but to facilitate the expertise in the room?” This changed my perspective.
Like coaches, leaders cannot be expected to have all the answers. But they must be patient and curious and ask meaningful questions to facilitate learning. Example: What is your approach now? Can you apply past experience to this problem? What does this situation teach you?
Finally, practice mercy and grace. This does not mean tolerating poor effort or careless mistakes. Rather, it means offering understanding and accommodation to someone who is not doing something exactly how you would do it.
Valerie had a bad approach that day with our CEO at the time. But if he had intervened, I would not have learned how to answer unexpected questions or later reflect on how to better prepare for executive presentations. If he had followed the advice, I would not have discovered my own true ways of development. To this day, I credit him with helping me develop the ability to present calm in dangerous situations. He is also the reason I have the courage to delegate to colleagues and team members even if it means watching them struggle. That’s the only way all of us — leaders and employees — grow.
