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Writer's pictureMichael Tooker

The Art of Doing Hard Things Graciously

Since publishing Grace at Work, the most common question I’m asked is, "Can you teach me how to do hard things graciously?" And by hard things, people inquiring generally mean things like dealing with relational strife between coworkers, confronting performance problems, or terminating somebody who hasn't performed well in a long time (often to the detriment of the team).

Man and woman having conversation

I have a doctor friend that years ago did his residency at the New Orleans County Hospital. He told me about a patient that came in with diabetes. The story is familiar but not to a young resident. The disease was eating away at the flesh of the obese man’s feet and maggots had taken up residence. The man nonchalantly acted as if nothing was wrong. However, when my friend looked down he couldn’t believe his eyes. How could something so heinous be seemingly hidden from someone with so much at stake? When people ask me how to graciously do hard things, this is what often crosses my mind. After 30 years in the workplace, it’s all too common that there’s something cancerous eating away at the organization—and while nearly everybody sees it—the leader is sadly turning a blind eye.


So can I teach you how to do hard things graciously? If we were playing golf, I’d tell you we’re on a long par 5 and it’s one of the more difficult holes on the course. So what I’ll do is offer a few tips to get you off the tees and down the fairway. In future posts, we’ll focus on the short strokes of this tricky topic.

The first step in doing hard things is to decide you’re going to do the hard thing. Sound simple? It is! However, many leaders never get this far. That’s why the problem goes unaddressed. Leaders often have so many competing priorities that unsavory problems requiring courage, endurance, and emotional energy often fall by the wayside. So if you want to do hard things graciously, start by deciding you’re committed to doing that hard thing.


The next step is to figure out the “graciously” part. And in my humble opinion, three things set you up to approach conflict graciously.


  1. For starters, don’t consider it a one-time event. Rather, assume you’re entering into a process. If difficult things were easy, you would have dealt with them. They’re difficult because there is often not an easy solution. Working through it will take time, and there’s likely an emotional cost you’ll have to pay to work it all the way through. Difficult things are rarely resolved in a single sitting. They take time. They take finesse. They require relational investment. Assume it will take time to wrestle it to the ground.

  2. Next, distill in your own mind what the problem is that you need to resolve. All too often when something is going wrong with someone, there are actually a whole bunch of things going wrong. Worse yet, when left unchecked, the problem is aggravated and over time every single thing about the person in question seems wrong. The reality is, there are usually one or two things that are at the heart of the problem. Before sitting down to address the problem, define and describe precisely those core issues. Issues that if addressed, will lead to a positive and substantive change.

  3. Now it’s time to sit down with the person and start a humble yet candid discussion. In this initial conversation, you do what I refer to as, “Hold up a mirror.” Meaning, you start by humbly and honestly sharing with them your reflections. The things you see that, while likely not perfectly accurate, are directionally accurate and describe a reality that you are not willing to allow to continue. A reflection that reveals a problem that must be addressed. Invite them into a conversation in which you mutually define and describe the problem, articulate that ignoring it is not an option, and agree to acceptable outcomes and necessary next steps.


So now you’re off the tee box and lying in the fairway. While this may seem oversimplified, my experience tells me that often these first steps never get done. As a result, problems persist and grow over time. If you can get as far as acknowledging there’s a problem, committing to address it, distilling it down to its core, and opening up a dialogue with the problem person directly … you’re well on your way to dealing with hard things graciously. If you have tips to help our readers do hard things graciously, please share them in the comment box below.

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