The Four Conversations You Must Get Right as a Leader


By Tracy L. Spears
June 10, 2019

Effective leadership starts with communication, and progressive leaders need to understand how to ensure that their interventions lead to positive outcomes. The good news is that most leadership communication falls into a few repetitive categories. This article focuses on effective one-on-one techniques. These are four conversations we must get right as leaders.

Tracy L. SpearsAlmost all successful leaders understand that effective leadership really comes down to influence: influencing outcomes, influencing direction, influencing decisions, influencing atmosphere, and influencing people. The degree to which a leader can successfully influence people and teams becomes the “lid” in his or her role. The only reliable tool we have to influence others is communication. Any leader or manager who is serious about improving his or her own performance should always start with improving communication skills and techniques.

Influential leaders are great communicators. They know what to say and when to say it. They also understand that effective communication is learned. It does not necessarily come naturally, and it needs to be worked on the same way a leader might work on his or her technical skills. We have all worked with would-be leaders who never seemed to get it right. They would say the wrong thing at the wrong time. Or worse, they would say nothing when something definitely needed to be said.

This is especially true in high-performance environments or in organizations going through significant change.


The Timely Talk is a must-have conversation for specific situations. No leader looks forward to a Timely Talk because of the stress associated with it.

How do you know it is time for a Timely Talk?

  • Someone is underperforming and affecting the overall results.
  • Someone is creating issues for the team (any kind of issue).
  • You are invested in the person, and he or she is not succeeding.
  • It is not going improve without your intervention.

Every situation is different, of course, but there are proven ways to have a Timely Talk. Most leaders will either avoid this dialogue or go into it without any preparation.

Top leaders know how to structure this talk for success. Your Timely Talk script should look like this:

  1. Explain the reason for the meeting (i.e., performance issue).
  1. This (issue) concerns me because . . .
  1. Confirm the employee’s understanding of the issue.
  1. Make a clear coaching recommendation.
  1. Confirm the recommendation and have the person repeat it back to make sure it was understood.
  1. Set up a review time and put it on both of your calendars. Clarify your confidence in the person.

The important thing to remember is that there are no open-ended questions with this exchange. If the issue is that the employee is consistently late, for example, never ask “Why were you late?” There is always a good reason (well, always a reason, anyway), and the reason will become the focus instead of the behavior.

Leaders often ask if this is the same as the sandwich approach, where you say something positive to start . . . stick in the criticism. . . . then end on a high note. That approach is outdated and manipulative. Don’t be afraid to jump right in to the issue. It’s more authentic, and your people will appreciate you not starting with something phony just so you can make your point.

 Remember, your #1 job as a leader is to develop other leaders. The Timely Talk is one of the many tools used for facilitating effective communication.


This one is so simple, yet very few leaders ever do it. Here is the summary:

  • You have someone on your team with amazing potential.
  • She is still learning and improving.
  • She may be hitting some bumps in her career.
  • You expect her to do GREAT things.
  • You need to tell her!

Leaving this person alone is risky. You have an opportunity to influence her growth and ultimate success. Not having the conversation is negligent. This is the Rock Star Reminder. It is an important as it is simple.


Every skilled leader has had this kind of dialogue, and none of them look forward to it. The leader needs to understand that the key to this conversation is timing. There is always stress and emotion involved, usually for both parties. If a leader has a “Now or Never” conversation too early, it will

feel like manipulation. If the dialogue happens too late, there won’t be enough time for the person to make the necessary changes. The timing has to be absolutely perfect. The Now or Never conversation should always follow a failed Timely Talk (#1). The person knows that the performance or behavior or other issue cannot continue and has had some time to make changes. This person is now at risk.

The best way to prepare for a Now or Never conversation is with talking points. Lots of different things can happen in this dialogue, so scripting your comments and questions is not the best way to prepare.

Here are some effective talking points that will take the conversation where it needs to go:

  1. We seem to be stuck, and we’re running out of options.
  1. You are making a decision about your future with your performance, do you understand that?
  1. Your potential in this role is as great as it ever was.
  1. This is the moment where things must change. 

This dialogue is the last chance a leader has to influence behavior. The Now or Never conversation is one that most leaders are unwilling to have. You can separate yourself from other leaders and managers with your candor and honesty.


As its name implies, the Stay Interview is the conversation you have with a proven and valued team member whom you very much want to stay. This important tactic is routinely overlooked, even in high-performing organizations. Do you want to surprise and impress your team with truly progressive leadership? Learn how to conduct the Stay Interview.

How Do You Know It Is Time for a Stay Interview?

The recommended strategy is to add Stay Interviews to your calendar. Quarterly works best. Every quarter you will consider the following:

  • Who on your team is really performing?
  • Who might be being overlooked?
  • Who is in a role that may have less recognition attached to it compared with other roles?
  • Who seems to have a lot of upside potential?

You are not really reacting to a certain accomplishment; you are paying close attention to sustained performance.

“Stay interview” is an internal descriptor to help you remember what you are doing and why. As far as he is concerned you are scheduling a time for a conversation with him about his position and performance.

Another important detail is that you do not want to schedule a series of stay interviews. These should be occasional and important one-off conversations. Doing too many or doing them too often will erase the positive effects.

How to Conduct a Stay Interview

The meeting should be set casually, and not as a part of a formal performance review. Ask the candidate if he can set aside some time for you on a certain day. Make sure your tone is upbeat and positive, and don’t set the time more than a day or two into the future. You don’t want this valuable person worrying for a week about a pending conversation with The Boss.

When the day comes, you will keep things very casual. The only formal part of the meeting will be your preparation. Start things off by thanking the person for taking the time to meet. Next, tell him you have been consistently impressed by his performance. Be specific here . . . be certain to note aspects of the candidate’s work that are excellent. For the people you are doing Stay Interviews with, this should be easy.

Tell him you want to ask him some questions about himself and his job, and that you would appreciate candid responses. You tone and body language will make it clear that he is in a safe environment with a leader who really values him.

Great Questions for Your Stay Interview

Here is a series of great questions for Stay Interviews. You will see a few that are very applicable to your situation and maybe a couple that are not. Add a few of your own questions to the list . . . maybe something specific to the mission or culture of your organization. Start off with general questions and then move to more specific topics:

  1. How are things going for you?
  1. Are you enjoying your work?
  1. What is the best part of your job?
  1. What is the part you enjoy least?
  1. If you could change something about your current responsibilities, what would it be?
  1. Do you ever have tasks to do that feel like a waste of time?
  1. Where do you see yourself in five years?
  1. Is there a task or process that is done outside of your responsibility that you think we could improve on?
  1. Is there something that you think we may be focusing on too much?
  1. Do you see any growth opportunities that you think we may be missing?
  1. How do you feel about our working relationship?
  1. Do you have any coaching tips for me?
  1. Do you know how valuable you are to this organization?

These questions, along with the additional questions you add to the list, will guarantee a positive dialogue with your candidate. You will have opportunities to ask for more detail and possibly hear some great ideas—maybe even do a little brainstorming. The last question will give you an opportunity to tell the candidate how much you appreciate them and their great work.

Your Stay Interview should take around 20 to 40 minutes. Any shorter and it wasn’t a substantive conversation. Any longer and you probably started talking about other people or went off topic. Twenty to 40 minutes is your sweet spot.

It would be hard to list all of the positive benefits of Stay Interviews. Many of the best outcomes will be invisible, but still powerful. You can strongly influence retention, culture, job satisfaction, expectations, working relationships, and much more. Adding the Stay Interview to your repertoire of leadership skills will you put you in a small group of progressive leaders who know how to pay the right kind of attention to the right people.

Now you know the four conversations you must get right as a leader. Using these templates, along with your own thoughtful preparation, you will see your positive influence over people and outcomes grow exponentially.

Remember, communication skills are your #1 asset as a leader.


Tracy L. Spears

Speaker, Author & Advocate

Exceptional Leaders Lab

(918) 779-7744

Topics: Leadership

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