Five Key Questions for Conducting Difficult Conversations

October 14, 2020

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Five Key Questions for Conducting Difficult Conversations

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Being a leader is not for the faint of heart.

While the stereotypical leader sits at a cushy executive desk peering out a vast wall of windows and collecting a generous paycheck, the reality is that most leaders carry a heavy load of responsibility. They are responsible, not only for the company’s bottom line, but also for the team that the bottom line supports and the clients the company serves.

Good leaders take this seriously. Others…well, they may, unfortunately, fit the stereotype.

But what happens when good leaders, in support of the company’s bottom line, must have a “difficult conversation?”

For example:

  • Marty, formerly a top sales associate, has not closed a sale in three months.
  • The first half of the year was an economic disaster due to the pandemic. Employees are not aware of the seriousness of the matter, but their individual livelihoods are at risk.
  • Susan is not communicating with others on the team, and, while she personally works hard, the goals have fallen behind because the work is not coordinated with that of others.
  • Mary has dropped some balls with regard to client agreement details, and now a lawsuit is threatened against the company.
  • Joe is not pulling his share of the load. The rest of the team has noticed and is starting to show resentment for having to bridge the gap.

Like it or not, in order to preserve the company, a leader must know how to have a difficult conversation.

But where do you start?

You start with asking some key questions.

1. Is it a CHANGE issue?

If you have a star player and, suddenly, their performance plummets, this is likely a “change” issue. Before you reprimand or release them, consider what the change may be and address it together with them. It could be that having one difficult conversation resolves the issue and allows them to get back to topside.

In the case of Marty, obviously, something recently changed that caused him to lose his edge. Was it a personal matter? Is the work no longer engaging? Or is he simply in need of a vacation because he spent day and night closing sales last quarter?

Taking the time to determine what changed will help you find a baseline issue to address together.

2. Is it a CIRCUMSTANCE issue?

Let’s just say that 2020 has been a “circumstance issue” kind of year. In making plans for 2020, companies could not have anticipated the one issue that would define their year: COVID-19. In fact, it was unheard of.

But it did happen. And now what do you do?

First, you have an honest conversation with your people. If you have to cut back, be honest with them. Rather than dragging out the inevitable, let them know what’s coming, help them all you can to find new work, and make the cuts you must make.

It could also be that, on learning that in order for some to stay on full-time, some would have to be released, your team could creatively determine the number of hours they could give up in order to keep a co-worker employed. Teams can add a great deal of passion and wisdom in challenging times, if you include them in the conversations.

3. Is it a CONFIDENCE issue?

You know Susan is excellent at what she does. But consider that maybe she doesn’t know it.

It could well be that her lack of confidence is what keeps her from communicating with the rest of the team before she is assured that something is “perfect.” It is a risk she does not have the confidence to take.

Having a difficult conversation, in this instance, could bring realization and healing to an otherwise excellent employee. And, done well, it can have restorative value as well.

4. Is it a CAPACITY issue?

If you have someone who is normally meticulous in their work, and they have begun to drop balls, consider how much work is on their plate. What may appear to be a carelessness issue may actually be a capacity issue.

Have a conversation to determine the root cause and to find ways to shift the load. Talking details may be a difficult conversation for a leader, but at times, it is essential to determining how to solve an issue.

5. Is it a CHARACTER issue?

One of the biggest issues a leader has to address is a character issue. If there are patterns of behavior that, despite numerous conversations, does not change, then you must have the difficult conversation of letting someone go. As a last resort, this may be necessary in order to preserve the team as a whole.

Bottom line, a difficult conversation is being able to communicate in a way that gets to the root of the issue. It can be uncomfortable for either or both parties to get to that point. But if it is done with respect and the goal of resolution in mind, it can have exponential impact, not only on the team or the company, but on the individuals as well.

For more resources on how you can increase communication, collaboration, and leadership across your organization, click here to learn about the Communication Impact Report and Workshop for leaders and their teams.

As the CEO of Strength Leader Development, Deb Ingino is a highly sought-after international executive mentor, coach, trainer, and speaker. Deb is well versed in global business operations and helps business leaders and their teams to discover and leverage their strengths, so they can create highly collaborative teams that deliver great results. With a refreshingly direct style, and using the Maxwell Method, Deb helps leaders and teams to deliver profitable results. Connect with Deb to learn more about her mentorship and coaching programs to equip you with advanced strategies to elevate your results.