Using Challenging Projects to Develop Effective Leadership Skills

by Michelle Hunter

How to get value out of difficult experiences.


Every new project presents an opportunity to grow. Every new client, audience, product, or situation presents “lessons” we can use to help us develop effective leadership skills. Are you intentionally taking advantage of these challenging moments to grow as a leader and develop more effective leadership skills? 

It took me a few years in the business “trenches” to spot my own growth opportunities. Like many people, I had difficulty balancing paid work with the important strategic tasks I needed to complete inside my business. I created marketing strategy and tools for clients, but struggled to find my own marketing voice and rhythm. I knew how to manage my time, but still couldn’t find enough time in my schedule to get everything done. Sound familiar? 

At the time, I didn’t realize I was actually in the middle of a lesson. My “failure” to manage my business well was a symptom of the need to develop effective leadership skills – both self-leadership skills and the ability to prioritize tasks, delegate, and inspire a team. The discomfort and stress I felt was an indication of the need to grow and develop as a leader. 

Leadership growth is an ongoing process. I’ve developed a few operating rules along the way to ensure I continue to improve. 

Rule 1 :: Intentionally select challenging projects. 

Some of the top gurus and motivational speakers advocate mastery and repetition. They tell leaders like me to stay in my lane, master my role, and focus my efforts on the projects that I can complete efficiently and well. I agree with this advice in general… and I know first-hand the draining effect of creating a new project or solving a problem in an area outside of my expertise. 

Unfortunately, there’s a problem with this advice – -> It’s pretty difficult to learn new things and develop new skills without taking risks. 

In my business, I balance security and exploration. I leave a little room for risk, and I intentionally select a project periodically that will challenge me and become a catalyst for my growth as a leader. Sure, there are opportunity costs to this approach. But, I believe the benefits of becoming an effective leader outweigh them. 

Challenging projects can be an exercise in self-awareness. I am never more humble than when I’ve worked diligently to solve a problem without actually finding an answer. I am most aware of skill gaps in my work when I’m struggling to do something meaningful. I embrace these moments, not as an opportunity for self-deprecating humor (although that happens at times) but as an indication of where to direct my future actions. 

Struggling to write a challenging piece of content? I need to improve my copywriting skills in this area. Not finding an answer to a business management issue in my organization? Time to seek a mentor, find a book, or take a class so I can learn more. Challenging projects shed light on areas of my own performance I might rather ignore. That light allows me to grow professionally… making me a better business owner in the process. 

Rule 2 :: Use challenging conversations to stimulate process improvement. 

Sometimes projects aren’t smooth. Relationships on the team get a bit tense at times, too. Projects run into trouble and I occasionally find myself in the middle of a difficult conversation with a client. Interaction with people is tough, and challenging conversations happen as a normal part of business. 

In the past, I avoided these conversations. Now I use them to improve my business and develop more effective leadereship skills. 

Problems are most often an indication that something needs to be improved. The process might be wonky or bloated. Written instructions and communication might be convoluted or obscure. Expectations might not match reality for customers, team members, or collaborative partners. If I can step away from the emotion of the situation and look at it objectively, I usually find an issue I can solve.

After the challenging conversation is over, I make time to reflect. Sometimes I do this alone in a journal or on a white board. Other times I gather key individuals and we reflect as a group. The goal is identifying lessons we can learn and issues we can address, so things are smoother and more efficient in the future. 

Rule 3 :: View questions as an indicator, not a problem. 

Can I just be vulnerable for a moment? Sometimes questions annoy me, especially when they are unexpected or occur when I thought everyone was on the same page intellectually or philosophically. Challenging projects are an incubator for questions, so you can see the problem here, right?

I expect questions when a potential client and I are discussing a contract. I anticipate questions during the copy revision process or when I’m educating someone on a concept that is new or foreign to them. But questions after I thought we had an understanding? I naturally react with frustration and a belief that the person asking must just “not care” enough to pay attention. Not good, folks. Not good. 

Questions can be a clue that I am not using effective leadership skills. Ouch!

Most people want to learn. They want to work effectively. They want to participate and add value.  Questions are usually not an indication of a lack of interest. More often they are a sign that I have not shared enough information, properly communicated vision, or provided clear direction. 

Maybe I went too fast and made inaccurate assumptions. Perhaps I skipped ahead or spoke in a vague way. Maybe I used terms that made sense to me, but left my team members, clients, or colleagues scratching their heads. In any case, those questions that annoy me are nearly 100% of the time a fault of my approach or my leadership. I choose to receive them as an indicator that I need to pause and identify missing elements and supply them. 

Clear communication and a willingness to pause and answer questions builds trust. My team functions better when everyone feels free to ask questions and seek clarification. My clients feel supported and engaged when their questions are answered with humility and insight. 

Growing as a leader means challenging yourself to expand your skills – both personally and professionally. 

There’s an old saw that says leaders are promoted until they reach a “level of incompetence” – meaning we stay stagnant at a given level until we are willing (or able) to master it. Feeling stuck as a leader? Wishing your business would break through an income plateau or achieve a new level of impact? Reflect on your ability as a leader. Maybe you need to embrace a challenge or two. 

Has your business outgrown your marketing strategy? Are you struggling as a leader to communicate vision to your team?  We should talk. 

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