April 4

A Leader’s Guide to Having Difficult Conversations


Sale Leadership Awakening
Sale Leadership Awakening
A Leader's Guide to Having Difficult Conversations

In this episode of the Sales Leadership Awakening Podcast, host Steven Rosen and Colleen Stanley delve into mastering difficult conversations, stressing preparation and agreement on the next steps. They highlight vital emotional intelligence skills essential for navigating these dialogues effectively. Practical strategies for delivering constructive feedback and fostering growth are shared, emphasizing the importance of stating intentions and fostering psychological safety.

“If this is an important discussion that we want to help someone get better on our team, taking the time to think it through, to prepare what you want to say, how you want to say it, if you have a coach or if you have a colleague that you can role play it through and see how it sounds, you’re going to get much better results.” – Steven Rosen

Key Takeaways:

  • Preparation is vital to having successful, difficult conversations. Thinking through what you want to say and how you want to say it can lead to better outcomes.
  • Emotional regulation is an essential skill for sales managers to develop. Managing your emotions during difficult conversations can help prevent them from escalating into arguments.
  • Empathy is crucial in difficult conversations. Understanding and acknowledging the other person’s thoughts and feelings can help create a more productive and respectful dialogue.
  • Stating intentions before giving feedback can help create psychological safety and ensure the feedback is received constructively.
  • Focusing on feedback and coaching when onboarding new employees can set the expectation that difficult conversations are a normal part of the company culture.

Follow Colleen Stanley on LinkedIn

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[00:00:05] Steven Rosen: Welcome to the Sales Leadership Awakening Podcast. I’m Steven Rosen, and Colleen Stanley is my co-host. 

[00:00:16] Colleen Stanley: Welcome, Colleen. It’s good to see you, Steven. We’re having a bright, sunny day here in Denver, Colorado. I hope you’re having the same up there in Canada.  

[00:00:24] Steven Rosen: I wish I could say the same in Toronto, but we’re still waiting for spring.

[00:00:28] Steven Rosen: As always, we try to bridge the gap between knowing what you should do and doing it. Today, we want to help you master the art of having difficult conversations, which we know most people will avoid. Over 50 percent of people avoid difficult conversations because they don’t enjoy it.

[00:00:47] Colleen Stanley: That’s correct, Steven, and it’s interesting. It’s not even based on personality style. So, a lot of times, we think that people who could be labeled as high drivers are really comfortable having those conversations. I know I have a lot of high drivers in sales roles and sales leadership roles, and they’re not comfortable.

[00:01:03] Colleen Stanley: However, here’s the good news. I know that you have five steps because we’ve talked about how you have coached your high-driver sales managers, who, even in that case, might be reluctant to give feedback. Maybe walk us through those five steps because frameworks are enormous on knowing how to execute bridging the knowing and doing gap.

[00:01:24] Steven Rosen: You Got it. I teach part of a course in bold sales leadership, and one of the components is being comfortable having difficult conversations because we know if we don’t have them, small fires become more extensive fires become infernos. I don’t know how many coaching clients have problems with a rep when I talk to them. I said, let’s go through this and discuss some ways you can improve.

Preparing for Difficult Conversations

[00:01:47] Steven Rosen: The first thing I have learned and shared is that you want to prepare for the conversation. There’s a direct correlation between how much you prepare and how well the conversation goes. As part of emotional intelligence, part of what you want to do, and you’re the expert on this. Still, part of what you want to do is seek to understand and make sure your message is being heard because sometimes people shut down when you’re having that conversation or they’re hearing something different.

[00:02:15] Steven Rosen: So once you’ve listened, it’s really about agreeing on the next steps because part of what you want to see happen is some change based on the conversation. One of the critical things that I may do differently, and I’m not sure if you do this, Colleen, but anytime there’s a plan of action required. Usually, the manager would write it down and send it to the rep.

[00:02:38] Steven Rosen: I invert that and have the rep send their plan of action to the manager, which does a couple of things. One, it crystallizes it. When you put pen to paper, it crystallizes in your mind. Two, it forms a much better commitment, almost like a contract you’ve written then your manager has written, and the last step is follow-up. It is a very simplified approach to running through and getting prepared and then making sure that what you said is heard and that you have an agreement and a plan in place.

[00:03:10] Colleen Stanley: A couple of things resonate here. One thing that I get from my sales managers is that we are all over our salespeople about pre-call planning, right?

[00:03:21] Colleen Stanley: We’re getting ready for an upcoming sales meeting, but when we reverse that and ask managers, how much time are you spending pre-call planning your one-on-one coaching, especially difficult conversations? Are you rehearsing the difficult conversation? You usually get a, ‘Uh… not so much.’ I think that’s one that I hope the listeners take hold of there.

[00:03:43] Colleen Stanley: Something else you said was quite interesting. The rep sends back the action item, and this aligns with what Dr. Robert Cialdini talks about in his principles of influence. I do not have it entirely correct here, but he teaches that people are more likely to honor it when they commit. So if [00:04:05] the manager is the one committing. I’ve made that mistake, so I’m having this big light bulb; you’re tying into a principle of influence that, hey, if I’m committing to the action, I’m saying I’m going to do this more likely that it will happen.

[00:04:19] Colleen Stanley: Those are two fundamental points that struck me today. 

The Role of Emotional Intelligence

[00:04:23] Steven Rosen: I take a very simplistic approach, but some of those little nuances make a big difference in outcomes. Tell me, Colleen, in your experience, what are some of the critical emotional intelligence skills that a sales manager needs to develop effectively to navigate through having challenging discussions with their teams, even with their boss, at times that they need to be able to have difficult conversations?

[00:04:45] Colleen Stanley: They align nicely with your description. Number one would be emotional regulation because even with well-intended conversations, let’s say you recall, planned it quite well, you might have a salesperson that gets a little defensive, and they start lobbying excuses.

[00:05:04] Colleen Stanley: Maybe they put the monkey back on your back, and so what can happen if we’re unable to manage our emotions as a leader? We get into those fighting for the need to be right rather than getting it right. A mentor of mine once taught me, and I think I’ve shared on our podcast before, that when you’re stable, you can do it.

[00:05:22] Colleen Stanley: When you’re stable, you can execute that framework you just talked about. You also mentioned listening, and I believe you said something about whether the salesperson actually hears what you’re saying. So, the skill there is empathy, and empathy is saying what that person is thinking or feeling, even if they’re not expressing it.

[00:05:44] Colleen Stanley: Active listening is repeating back, but empathetic listening is a whole higher level of listening because, to your point, if I don’t maybe start the coaching conversation with, hey, listen right now, you might be thinking this, this and that. Let’s say not putting things into your CRM. Have you ever heard that one before, Steven?

[00:06:03] Steven Rosen: I have to tell you that many sales managers struggle, especially with good reps who give them the excuse that, you know, I’m doing a good job, I don’t have time.

[00:06:13] Colleen Stanley: The empathy comments always depend on each individual conversation, but they could say something like, Steven, right now, you’re wondering why I’m always writing about the CRM.

[00:06:23] Colleen Stanley: You know, you’re hitting your numbers. Why don’t I go bother somebody else? You might be listening today and saying, ‘Well, that doesn’t sound like a very professional language.’ Empathy is saying what the other person is thinking or feeling because, to your point, if we don’t, they keep fighting your advice. So that’s why if you can demonstrate empathy first, even in a difficult conversation, you can be assertive.

[00:06:50] Colleen Stanley: And that’s what you’re talking about—laying out the plan and agreeing to it. Because I’ve seen people do the okie-dokie thing when they get emotionally triggered. I’m out of here. Let’s have this conversation in 10 years so they don’t finish your framework plan of action. 

[00:07:07] Steven Rosen: And you get the head nodding, saying, I’m not hearing you, but I’m pretending to.

[00:07:13] Colleen Stanley: Exactly, and they’ve got this little weird smile where they’re nodding their head, but they’re thinking, I’m not doing a thing you’re talking about. Absolutely. 

[00:07:22] Steven Rosen: All right. All right. Disagree. Right? That’s a great point, and I think it augments well because of resistance. Sometimes, the manager going in is concerned about having resistance, and once the resistance appears, then how does the manager manage their own 

[00:07:39] Colleen Stanley: Emotions? Yeah, exactly. It always starts with you because I’m the only one who can manage the trigger. But empathy—it’s amazing when you really know how to use it effectively. Real-world empathy diffuses the conversation.

Constructive Feedback for Growth

[00:07:54] Colleen Stanley: With that said, we’ve got emotion management. If you and I step into a sales manager’s head, here’s what they sometimes think about feedback: ‘I’m going to have fallout here. A person’s going to quit. It’s going to affect my team dynamics. I want to be able to give feedback to a member of my team while still maintaining a positive culture.’

[00:08:15] Colleen Stanley: How do you coach a manager to pass those fears that can be perceived or real? 

[00:08:21] Steven Rosen: I like how you just framed it because one of the things you just twigged a thought here is that if you perceive the conversation as problematic. It is. In terms of hiring, and I’m slowly going a little bit off track here, in terms of hiring folks, one of the things we look for managers is comfortable having difficult conversations. We have a framework of preparation, good listening, and maybe a way to close it up because of natural discomfort or avoidance. 

[00:08:50] Steven Rosen: One way to mitigate risk is to continuously be honest and open with all your reps because then people expect you to provide that feedback. If it comes, let’s say, review time, and you haven’t offered that feedback throughout the year, it will be like a ton of bricks falling on the person. 

[00:09:07] Steven Rosen: So part of that role comforts you that if there’s something you spot as a manager, you see if you believe that feedback is a gift if you’re empathetic if you listen to what the person’s saying back, and if you’re not being defensive.

[00:09:22] Steven Rosen: One of the overriding things is that if you see it as a difficult conversation, guess what? It’s going to be, you know, perception becomes reality. We talk about preparing to mitigate the risk of team dynamics. Well, one, you want to manage these discussions one-on-one, but you don’t want someone going off and saying, ‘Oh my God, Colleen was tough on me.’

[00:09:42] Steven Rosen: Two, feedback is a gift. If we look at it as that and the individual looks at it as that, I think we can mitigate some of the risks of fallout. How we handle those conversations has a significant impact on how we turn around performance or how we get people on board to where we need to go.

[00:09:58] Colleen Stanley: Exactly. Exactly. Good points. 

[00:10:01] Steven Rosen: Regarding difficult conversations, the feedback component is critical in how we give feedback, and sometimes, as I just said, it’s not received well. Can you talk about some strategies you coach your folks on to ensure that the feedback is constructive and leads to growth or change rather than someone feeling, ‘Oh, my God. I just had a ton of bricks dropped on me?’

[00:10:24] Colleen Stanley: I’m going to return to the point that the presenting problem is never the real problem.

[00:10:30] Colleen Stanley: We’re thinking about the difficult conversation; that’s where the challenges lie. But we can prevent that something you said; examine your hiring process. When you hire someone, they come into the office with two briefcases: the visible, the resume, and the invisible, and the invisible, which is often the soft skills, how they react to feedback.

[00:10:51] Colleen Stanley: I would encourage and challenge sales leaders listening today. Take a look at your interview guide. How many of the questions you have are vetting that candidate for when they receive feedback? Secondly, [00:11:05] did they even apply it? Secondly, I’ve been encouraging many people to do what I didn’t even think of, Steven, until this year: feedback and teaching feedback must be part of the onboarding process. It could be a value at this company: we care, and when we care, we share. When you look at it in life and care about somebody, you share. But somebody keeps reacting and responding; there’s a point where you go into apathy.

[00:11:31] Colleen Stanley: I’ve shared with many people who have worked for me when I go into apathy; that’s when you should be worried because I don’t care anymore. I’m not going to care enough to give you feedback. I think you can walk them through your 5-step framework. It doesn’t have to be a secret, so they know this is how we roll. There’s no secret there. So I think the onboarding. 

[00:11:48] Colleen Stanley: Then I think one final point. It’s always necessary for every conversation to state your intent and remind them of my intention in giving this feedback because I know it can make your life easier. I know this isn’t the person you want to show up with at work.

[00:12:05] Colleen Stanley: Stating the intention is also a great way to create what the term is today: psychological safety. Those are some ideas there. 

Bridging the Gap: Belief Systems and Preparation

[00:12:11] Steven Rosen: Yeah, those are some excellent ideas that show that you care. My first-ever coach, Pat, used to say, give them the WIIFM. What’s in it for them? In many cases, we’re giving feedback or having that conversation to help the person be perceived better and perform better. Part of it is you’re not doing it to make yourself better or feel better. Maybe it does indirectly because it’s off your chest, but also to help the individual, and I think part of that success component is what’s your intent going in.

[00:12:45] Steven Rosen: Everyone knows that they should have those conversations, right? But many of us avoid them. I know I’ve coached many folks who avoided that discussion.

[00:12:54] Steven Rosen: Sometimes my kids, I help coach them to avoid that discussion they want, but they don’t know how to have it. So, if you were to leave our audience with one perfect nugget on how to bridge that gap between knowing that they should have those conversations and actually doing the Nike thing, just doing it.

[00:13:14] Colleen Stanley: So, I would say, examine your belief system. Do you believe sharing is caring? Do you think that coaching can transform people? That’s when you’ll be ready to do the hard work of leadership. I mean, that’s why you signed up for this role. I had a mentor of mine, Steven, over 20 years ago, and I’m going in for my performance review; I’m the VP of sales and thinking easy-peasy.

[00:13:44] Colleen Stanley: We’ve had a great year, and this gentleman still mentors me today. He said, ‘Colleen, I never doubt your work ethic. You’re the first in, last out’, and then, ‘However, something has to change. You come into this office; you don’t look left to right. I’m unsure if you’re saying hi to your assistant anymore. It’s got to change.’

[00:14:04] Colleen Stanley: I was appalled and angry. I was like, ‘I’m giving my blood for this company.’ Guess what I’m talking about, 20-some years later? His feedback made me sit back and recognize that I was getting so task-oriented that I was forgetting the people side of the business. That was a gift, and that’s why I feel so strongly about it. It was a turning point for me, and you can believe it after that.

[00:14:30] Colleen Stanley: I watched my hurried and harried approach, which I still see with many people. You can’t be hurried and harried when you’re giving feedback. 

[00:14:36] Steven Rosen: How about you? First of all, it is very sage advice, and if anyone I know interacts before they get to business, it’s you. Whatever that advice you got some 20-odd years ago, when you were 10, really paid. 

[00:14:47] Colleen Stanley: off. It’s compounding. It’s a gift that keeps compounding. 

[00:14:51] Steven Rosen: It’s like compound interest. Exactly. So, from my perspective, if I were to share one thing, it’s a simplistic view, but there is a direct correlation.


[00:15:00] Steven Rosen: If this is a critical discussion that we want to help someone improve on our team, taking the time to think it through, to prepare what you want to say and how you want to say it, and if you have a coach or a colleague who can role-play it through and see how it sounds, you’re going to get much better results.

[00:15:19] Steven Rosen: It’s going to come off smoother. You’re going to be more confident in delivering it. If anything, we do, and I know everyone’s busy, and we’re rushing from one meeting to the next. Still, we know we’re having an important meeting with someone, taking some time to put some notes down, to think what the other may say or how they’re feeling before really meant a more robust discussion, and I believe the individual can see that. So, if you want to influence and have those conversations confidently, the key is preparing, re-preparing, role-playing, and practicing it because practice makes perfect.

[00:15:51] Colleen Stanley: It does. I had to learn that, Steven, where I had to have self-awareness, something I perceived as a difficult conversation, you may not.

[00:16:01] Colleen Stanley: And that could be going back to your childhood, some past event you had. I realized I had to rehearse and thought it was the craziest thing. Then I realized I could be saying the right words, but my facial expression was off, and my tone was terse. I’m with you. 

[00:16:18] Steven Rosen: Maybe I’ll share a quick story here. When I was a sales manager, it goes back a few years. I had a rep, and I won’t mention his name because he may be watching, but every year, he thought he should have won the sales rep of the year award. Okay. He was a nice guy and worked hard, but he was very pigheaded.

[00:16:35] Steven Rosen: You wouldn’t listen. Going in for his performance reviews, I would know there’d be resistance, and we would go on forever because sometimes those hour meetings become two-hour meetings. Yes. Yes. I remember that part of it was sometimes that you had to stop those meetings because you were not getting anywhere with the individual.

[00:16:53] Steven Rosen: How I used to end that, and I hope people find it funny because I just thought of it now, it was a long time ago, but I used to say, ‘Ask your wife if what I’m saying is valid’ and almost like clockwork, he’d call me the following day and say, ‘Yes, I spoke to my wife, and you’re right on. I’m sorry’. That was like, oh, it’s desperation. You’re not listening; it was the same thing every year. I think I managed them for about three years.

[00:17:20] Colleen Stanley: The go-ask-your-wife technique.

[00:17:22] Steven Rosen: My insight is one: come to the table prepared. 

[00:17:26] Colleen Stanley: Absolutely. We hope everyone has enjoyed our conversation today and not only enjoyed it but learned some tips and tools for holding those problematic conversations because when you step up to leadership, you will have a few of them.

[00:17:40] Colleen Stanley: Even if you manage and lead an excellent team, you’re still a good person because we manage human beings. Thanks everyone for joining us!

[00:17:48] Steven Rosen: Thank you. It was a great session!


Colleen Stanley, emotional intelligence for sales and sales leadership, executive sales leadership, knowing and doing gap, sales leadership, sales leadership coaching, sales leadership development, sales management training, Stanley, Steven Rosen, the sales leadership awakening podcast

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