Conquer Leadership Challenges with Small Wins

When was the last time you felt overwhelmed by significant leadership challenges? 

There is no path to the end goal that doesn’t start with a small win.

Some of my recent work has included supporting leaders who have found themselves in such a place. What I often tell them is there is no path to the end goal that doesn’t start with a small win.

Can you relate to any of these scenarios?

• Boldly declaring an organizational commitment toward impacting injustice and inequity
• Addressing an underlying current of passive-aggressive staff discontent
• Rebuilding trust in a broken relationship with a key stakeholder, client, or employee
• Successfully navigating a challenging selection process, getting the job, realizing the magnitude of the challenge ahead, and wondering where to start
• Being the one shoulder-tapped to go in and “clean up” someone else’s mess

If you have been in a leadership position for any length of time and you work with humans, I’m sure that similar situations come to mind.

Breaking Challenges Down Into Small Steps

At some point, there is a need to step back, analyze the situation, and develop a plan of action. Speaking to that process is a blog for another day . . . but let’s say you have a plan but are feeling overwhelmed by the challenge ahead. You don’t know how things are going to work out and are maybe sensing a little self-doubt, wondering if this time you bit off more than you could chew.

After my retirement as a school board superintendent, my wife and I embarked on the 800 km Camino de Santiago. The trek took us from Saint-Jean-Pied-de-Port in France, over the Pyrenees, and clear across Spain over the course of 30 days. It was daunting to stand at the threshold of an 800 km walk and wonder if we had what it takes to execute our plan. The longest hike we had done before the Camino was three-days (at half our age) – we had virtually no experience taking on this kind of mammoth challenge.

Here’s the thing though: a 30-day hike is actually a whole bunch of one-day hikes, and we’d already done lots of those. And if covering 25 km in a day seems daunting, the reality is that it’s just a bunch of 1 km hikes.

Gain Momentum through Small Wins

The lesson here when facing a leadership challenge is to take the first step and go for an early small win to build on. Don’t focus on the ultimate goal – focus on the one thing you can do well to start you on your way. Make it to lunch, and then make it to your first auberge! It is both obvious and profound that there is no pathway to Santiago de Compostela that doesn’t include getting through day one.

Don’t focus on the ultimate goal – focus on the one thing you can do well to start you on your way.

Consider this reminder from The Power of Habit author, Charles Duhigg:

A huge body of research has shown that small wins have enormous power, an influence disproportionate to the accomplishments of the victories themselves. Small wins are a steady application of a small advantage . . . Once a small win has been accomplished, forces are set in motion that favour another small win. Small wins fuel transformative changes by leveraging tiny advantages into patterns that convince people that bigger achievements are within reach.

My first appointment as a department head came at a pretty young age, after a process where a number of internal candidates were overlooked. I was brought in to signal change, and one of my first strategies was to find something small (cosmetic, benign, low cost) that I could implement quickly that would fix an annoyance or frustration staff were feeling. This would signal that I was there to help, to support, and to make things better.

It may sound silly, but I noticed that the staff lounge windows were covered with faded construction paper to create privacy, so I installed proper Venetian blinds in the windows. You would think that I had brought in a hot tub! The yield was disproportionate to the investment. What an easy, quick, and small win to build on.

Lean into the Bigger Leadership Challenges

A significantly more daunting leadership challenge is to gain traction on an organizational commitment to any action connected to social justice, equity, and inclusion. Where do you start when internal leaders don’t know what they don’t know, are relatively unaffected by inequity (arguably, are even beneficiaries of it), and are primarily responding to a trend rather than a deeply held conviction? How do you even begin to move the needle in that situation?

It starts with remembering that success is the sum total of a bunch of small wins. There are probably ten significant challenges just to get to the starting line of that journey. Pick one and lean in, do it well, and leverage it for momentum as you start on the second – that’s what small wins are all about. Maybe it starts with giving voice and airtime to one story of inequity experienced by someone connected to your organization; perhaps it means leveraging the one respected leader who really does get it; maybe it’s initiating an equity audit or bias-awareness training; or it can simply be standing up to one racist taunt in the lunch room.

Whatever the next step is, lean in hard and do it well.

Whatever the next step is, lean in hard and do it well. And remember, overcoming any leadership challenge always starts with a small win. Do it, learn from it, capture it, and leverage it so that the next win builds on the first.

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