Gary Winters

Coach  Workshop Facilitator Author

When difficult conversations happen to good leaders

We’ve all been there. Leaders face “difficult conversations” all the time. Do any of these sound familiar?

  • You have to deliver a performance evaluation to someone who’s been under-performing for years, but the previous manager never confronted the situation
  • You’ve just been promoted to lead a group of former peers and one of them wants assurances that nothing will really change between the two of you
  • You’re getting tired of your boss interrupting you in meetings
  • You need to tell a peer that you feel you’re not being consulted or considered in cross-functional team decisions
  • You have substantial questions about a subordinate’s judgment in terms of how they handled a recent situation
  • You want to make an appeal for more resources (financial, human, technological, etc.) and the climate is all about trimming the budget
  • Someone wants to “triangulate” with you – they want to complain, gossip, vent or whine about someone else who isn’t part of the conversation
  • You have to tell a subordinate why you won’t be supporting their candidacy for promotion
  • You have privileged information and a subordinate is asking for advice which you really can’t deliver without revealing the confidential information

Difficult conversations have at least three things in common:

  • High stakes
  • Strong emotions
  • Unsure outcomes

And all too often, they come as a surprise and pop-up unexpectedly (had any unexpected phone calls from an irate customer or client lately?)

What do many people do when faced with a difficult conversation?

  • They procrastinate hoping the situation will resolve itself
  • They try to be subtle and in-direct to avoid hurt feelings
  • They jump to sarcasm
  • They suffer in silence
  • They stumble through the conversation convinced they will screw it up
  • They blame the other person for the issue and feel righteous indignation

The problem with these strategies is not that they don’t work, but rather that sometimes, they DO work.

That becomes what the psychologists call an intermittent positive reinforcement, which is powerful. It’s what drives people to play the slot machines even in the face of overwhelming evidence they are likely to lose because, every once in a while, they win.

There is a better way. You’ll need three things to navigate these white waters successfully.

  • Capability – good communication skills, both in terms of framing your message, and hearing theirs
  • Commitment – a genuine desire to create a positive outcome
  • Courage – a willingness to acknowledge your fear, lean into your discomfort, and go forward anyway

Let’s have a conversation about what works – and what doesn’t – when you’re having a difficult conversation.

“What ELSE Your Boss Never Told You” is the sequel to the very popular “What Your Boss Never Told You.” Packed inside are more tips, techniques, and insights about the challenging, but rewarding leadership position.

“What ELSE Your Boss Never Told You” is written in a conversational tone, as though you and the author were enjoying a cup of coffee and talking about the issues that emerge for new leaders. It stands alone, and/or could be read before or after the first volume, “What Your Boss Never Told You.” You can start with any chapter and read in any order you like.

if you search for a book on management, you’ll find a staggering 600,000+ books currently available. How can you narrow that down? “What Your Boss Never Told You” is the best place to start.

No textbook here – this book is short and sweet. It’s designed to help you “unpack” your new job and be effective from the first day with your new team. It contains twenty-one chapters filled with the wisdom Winters has gathered from real managers – effective, successful leaders in organizations much like yours.

Leaders make decisions every day – big and small. Most know that if they include others in the decision-making process, the quality of those decisions – and the commitment to them – will likely improve. That said, they also know it’s impractical, if not impossible, to include others in every decision they confront.

“To Do or Not To Do” tackles the question of when to make decisions on your own, and when to involve your team. It gives you a deceptively simple but proven method to determine, when you are facing a difficult decision, how to decide how to decide.

Far too many meetings are dreadful, mind-numbing, energy-draining, productivity-sapping, colossal wastes of time. As someone once said, “To kill time, a meeting is the perfect weapon.”

Here’s the deal: if you’re willing to learn and apply the techniques in “So, How Was Your Meeting?”, you’ll call fewer meetings, while vastly improving the ones you do lead. They’ll take less time, have more balanced participation, produce better decisions, and result in concrete action items for follow-up afterwards.

While there are thousands of books written for people about to retire, this may be the only book for people who manage soon-to-retire employees. Written in a casual, conversational style, “Managing the Soon To Retire Employee” will give you everything you need to know to move forward with confidence and grace.

You can be successful with Sooners. It won’t happen by chance, and it’s not a matter of pulling some management “trick” out of your hat. But you can learn how to do it, and you can apply what you’ve learned right away.

Managing friends or former peers can be awkward. When you become the boss, everything about these relationships can suddenly be uncomfortable. There’s a new set of ground rules to establish – as manager, you are going be accountable for the work performance of friends or former co-workers on the team, and they are going to have to adjust to the fact that they now report to you. Everyone involved can feel awkward and hesitant about the future. 

Have you been approached by management with an offer to promote you to supervision? Or, are you mulling over the possibility for the future? Find yourself not sure whether to accept the promotion?

If so, you’ve come to the right place. Help! They Want to Make ME a Supervisor will help you sort out a very big question: Should you accept the offer to become a supervisor? Once you’ve read this book, you’ll be confident that you’ve made the best decision for you and for your organization.