How to Turn Difficult Conversations into Productive Outcomes

Recently, I was on the phone with a CEO who called me seeking some advice.

"I have a few senior leaders whose actions are counterproductive to what we're trying to accomplish within the firm..."

"What do you think needs to be done?", I asked.

We had some productive conversation about their options...

"Well, I'm not ready to do something now but I might have to in 6 months."

That conversation made me reflect on a common trend I'm seeing within the companies I'm advising and a common question I'm asked in these newsletters and on LinkedIn.

I'm noticing hesitancy (and maybe a lack of clarity on how) to have difficult conversations—even though people know they are needed.

They know there's something wrong, they often know the culprits, and yet nothing is done.

Look, it makes sense. They are called difficult conversations for a reason... Even after hundreds of them, they can still be difficult for me.

But here's the reality... your ability to have effective difficult conversations that create productive outcomes is critical to your success as a leader.

Today, I want to share my formula for approaching these difficult conversations so you can start using them to create productive outcomes to further your team or organization.

How do you know when it's time?

This is often the easiest part of the formula.

Most of the time, you know. You can sense it.

Signs might include...

• You're finding yourself complaining about a certain individual and their actions

• You're noticing someone's actions are counterproductive to executing strategy

• You're receiving complaints or comments from other team members about someone's actions

• You can sense (or are receiving outward) resistance to plans or ideas that are core to executing strategy

Most of the time, you know.

You know who the conversations need to be had with and you likely know what the basics of what the conversation needs to be about.

So, what gets in the way?

Don't ignore the hidden costs...

We often avoid having necessary difficult conversations out of fear.

I've shared a few times about a story where I waited 5 years to have a difficult conversation with someone out of fear of what might happen and how they might react. I still regret it to this day.

We often fear we're going to hurt someone or negatively impact them in the short term. It's a fair fear! No one wants to hurt someone else.

We often think of the negative costs of having a difficult conversation—and we tend to focus on the short-term effects, in particular.

"What is this person going to think during the conversation?"
"How are they going to respond in the moment?"
"What's going to happen directly after the conversation?"

What about the cost of NOT having the conversation? What about the long-term effects of NOT addressing something that needs to be addressed?

That story where I waited 5 years to have a difficult conversation with someone?

I cost that person 5 years of their professional life.

I cost them growth. I cost them opportunity. I cost them the potential to find an organization where they could thrive.

There's an immense cost to the person and to the organization when we put these difficult conversations on the back burner.

Sure, there's tons of 'what-ifs' when it comes to negative outcomes...

AND, what if the conversation goes really well?

What if there's a foundational misunderstanding or communication error that can be resolved?
What if you're able to identify a growth opportunity for the person and they are better off for it?
What if you're able to effectively address something and the organization benefits?
What if you uncover an underlying difference in beliefs and the person has the opportunity to find another organization where they can thrive?

There are numerous positive outcomes for you, the person, and your organization that can come from having a difficult conversation.

So, sure, you could wait 6 months... but imagine all the good that could be accomplished in the next 6 months if you do it now?

Shift your mindset to think long-term and the benefits can become more clear.

How to make it as productive as possible.

When it comes time to have a conversation with someone, there are a couple of things to consider that make it more likely the conversation will lead to a productive outcome:

The Arena

Save these conversations for private 1 on 1 meetings. There's a time and a place to have a difficult conversation and a public setting with other team members is not it.

The Delivery

Perhaps my most important tip when it comes to these conversations is to focus on the goal, not on you.

Refer to the strategy and the person's role in executing the strategy.

Why is the strategy important?
What's at stake for the team or organization if we aren't able to execute strategy? Why is their role important?
How are they currently detracting from achieving the larger vision?

It's about the team and the strategy, not about wanting them to do something for YOU.

Be objective. Be tactical. Be specific.

The Balance

Difficult conversations are called conversations because they are meant to be two-way discussions. Both sides are meant to be actively involved.

Listen. Be patient. Be curious. Be willing to hear the other person out.

Sometimes a little direct, back-and-forth communication can go a long way to resolving what can feel like a larger conflict.

Productive doesn't always always feel positive.

As I close out this email, I want to remind you that the goal is to have a productive conversation.

Sometimes, productive may feel positive—like gaining a new mutual understanding or alignment toward executing strategy.

Other times, productive may not feel positive in the moment.

Sometimes a conversation can be productive because it may uncover the realization that someone isn't the right fit for their role or for the organization.

Although it may not feel too positive in the moment, that can be an extremely productive outcome for all parties.

Remember, there is a cost to each day you delay initiating one of these difficult conversations. Ultimately, great leaders are able to make these conversations (no matter how difficult) productive. Not easy...but productive.

Whether this email shared a different perspective or simply served as a reminder to do what you know you need to do, I hope it helped.

If it did, let me know what stood out to you.

If you're still finding yourself stuck, feel free to use the contact form to share more about your situation and I'll see if I can help you navigate your unique situation.

With intention,
Alan D Whitman