Summary.    When you see an employee struggling with a task you could do easily, it’s only natural to want to step in and help. But from the other side, this can feel more like micromanagement than support. And when leaders over-function by keeping too much...

“How are you justifying the sales and expenses estimates?” the CEO asked. My face glowed red as I stuttered. My heart rate skyrocketed and my throat tightened. I looked at my boss, Valerie. She made eye contact, held a soft gaze, and said nothing. 

She could have eased some of the heat directed my way by chiming in and saving me, but she didn’t. That’s because I had asked Valerie for an opportunity to present to our organization’s leadership team. Prior to the meeting, she’d informed the head of our banking division and the CEO that I was taking on this stretch assignment and that she would be an observer. So, instead of taking over from me when I was facing tough questions, she let me figure my own way out of the discomfort. I did muddle through it, albeit not as well as I would have liked, but in a way that left me better prepared for my next meeting with him.

I remember Valerie as a good boss because she often gave me developmental opportunities like these. The stakes were usually low like that small, internal meeting, where everyone knew I was still green and would be supportive. Valerie was present but in the background, allowing me to succeed or stumble but learn from the experience either way. Afterward, she never gave me long lists of suggestions on how to improve. Instead, she 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 both to help them grow and create a collaborative, empowered, productive team. But, faced with real workplace demands, it can be tough to put this into practice. Many of my clients say things like “I’m the only one who can do the job” or “If this project doesn’t go smoothly, the whole team will suffer.” 

Empathy can get in the way, too. When you see an employee struggling, it’s only natural to want to step in and help. But from the other side, this can feel more like micromanagement than support. And when leaders over-function by keeping too many tasks, they allow their teams to under-function. 

Here are some strategies you can use to make delegation easier.

Shift from doer to leader mindset

In my corporate job, we promoted the best doers into leaders. This came with an assumption that they would magically shift from being good at and motivated by performance excellence and rewards to excelling at and caring deeply about developing others’ potential. The mindset shift may be the hardest part of all. So, how can you facilitate this in yourself?

• Notice your payoff from doing. The thrill of achievement provides a quick dopamine hit. But that’s something you need to resist to get to the greater fulfillment of having helped others improve. 
• Claim your leadership identity by getting clear on values. Ask yourself: What three words do I want people to use to describe my leadership style? For example: Do I want to lead with control, urgency, and expertise? Or, with patience, curiosity, and empowerment? 
• Be intentional about responding, not reacting. In the moments where you are triggered to step in, ask yourself:  Would that be aligned with my values and who I want to become as a leader? 

Embrace the discomfort of the learning process

Many leaders tell me that, after witnessing an employee falter, taking back the work felt like the most supportive thing to do. I’ve felt this tension too. But Valerie taught me the power of holding space for struggle. Yes, this creates discomfort for both leader and employee because it’s a new way of working for everyone. However, as Gallup reminds us, one of the keys to engagement at work is the opportunity for stimulating challenges. And when you push through the struggle, the result is growth for all parties. 

How can you embrace, rather than resist, the discomfort of learning?

• Name your emotions, which according to psychologist Susan David, offers clarity and resiliency and can empower you to respond in an intentional way, aligned with your values.
• Normalize being uncomfortable. Neuroscientists know that these are the periods in which learning happens and perseverance is developed. 
• Reframe the situation. One potential reframe is: “I was allowed to struggle and that’s where I gained confidence in my skills. So I’m going to give my employee the same gift of time to solve the problem on their own.”

Distinguish between high- and low-stakes tasks

Leaders often tell me they remain stuck as doers because employees make too many high-impact mistakes that require intervention. But this usually happens when the bosses themselves hold on to all the work for far too long and are then forced to delegate at the wrong moment. The key is to instead hand off tasks when the stakes are low and missteps tolerated, or even expected.. 

What makes an environment low-stakes? Failure will support learning more than it would hurt reputation. Mistakes will not impact team or company success. The environment is safe for stops and do-overs. The people involved have support and compassion for less experienced colleagues on learning curves.

To know which tasks are ripe for delegation, consider ones that now feel easy or rote to you but would be good development opportunities for those on your team? Also think about work that drains your energy and doesn’t align with your skills, talents, and strengths but might excite and feel like a perfect fit for 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 like conducting a client meeting. Or, if they want to get better at influencing others, challenge them to get buy-in from a small team on using a new tool or work process before asking them to persuade your whole division to implement it.    

Be curious and facilitative 

Early in my corporate career as a trainer, people told me that I was visibly nervous during sessions I was leading. I explained to my boss that I was worried about not having answers to participants’ questions. Her response: “What if your role isn’t to have all the answers but to facilitate the expertise in the room?” This changed my perspective. 

Like trainers, leaders can’t be expected to have all the answers. But they do need to have patience and curiosity and ask insightful questions to facilitate learning. For example: What has your current approach been? Can you apply past experience to this problem? What is this situation teaching you?

Finally, practice compassion and grace. This doesn’t mean tolerating poor effort or careless mistakes. Instead, it means offering understanding and accommodation in the face of someone not doing something exactly how you would do it. 

Valerie’s approach that day with our CEO didn’t feel good at the time. But had she intervened, I wouldn’t have learned how to respond to unexpected questions or later reflected on how to better prepare for executive presentations. If she’d followed up with advice, I wouldn’t have discovered my own authentic ways of improving. To this day, I credit her with helping me to develop the ability to present calmly in high-stakes situations. She’s 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 that all of us — leaders and employees — grow.