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Home » Coaching Difficult Employees: 10 Questions For Increased Productivity
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Coaching Difficult Employees: 10 Questions For Increased Productivity

Press RoomBy Press Room29 December 20245 Mins Read
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Coaching Difficult Employees: 10 Questions For Increased Productivity

Coaching is the new leadership.

While “leadership skills” have dropped out of the top 20 soft skills on résumés, coaching is one way to help employees to feel empowered, valued and seen. A new Forbes council post points out how coaching is designed for the future of work – and its challenges. Working with thousands of coaching clients over the last decade, I’ve discovered what can open up the leadership conversation inside of tough times. Perhaps even more importantly, what I’ve learned from my own coaches has helped me to collaborate on nine books since the pandemic – transforming my relationship with productivity. When dealing with difficult team members and performance is lagging, here are 10 coaching questions that can change your results.

In my book, Easier, I focus on the coaching conversation – sharing how difficult employees let unnecessary sensitivities and drama cloud their judgment. For troubled team members, conflict outstrips collaboration. Difficult employees are unable to internalize clear direction and implement it, because they are unable to get out of their own way (or their own head). Can you relate? To be clear, these challenges are human qualities that we all share – because sometimes we are the difficult employee! Harvard Business Review says that coaching can “facilitate problem-solving and encourage employees’ development by asking questions and offering support and guidance rather than giving orders and making judgments.” Is it time to move beyond command and control, and change the conversation?

If empowerment, ownership and innovation matters to you, consider how these 10 questions can incorporate coaching into your productivity.

  1. What else could this mean? When someone is interpreting behavior or circumstances in a way that is not productive, asking for a new perspective is the first step towards new possibility. Another variation is, “What else could this be?”
  2. What’s good about this? Ever sat in a one-on-one that turns into a total b*tch session, where your team member uses the time to air out complaints and problems… instead of solutions? Reframe that conversation around discovery – and don’t buy into the idea that “the sky is falling”. Every company has problems and challenges – seeing obstacles as opportunities is key. Don’t dismiss a dilemma – reframe it.
  3. What are you making up, right now? When relationship issues surface, or dissatisfaction arises around work, human beings naturally create stories to process circumstances. How you frame the question is as important as the question itself: we all have interpretations of the world around us. The question is, are those interpretations useful….and real? Because coaching deals with what is-not what is made up inside our heads.
  4. What are you forgetting? Wyn Morgan is a former coach of mine, and he shared this powerful idea of a common forgetfulness that we all share – as well as question number 3. So many times, I forget that I am capable, resourceful, and resilient – my coach reminded me of those facts! Instead of finding fault, remind your team that they can rise to the challenge. In my experience, a situation is never tougher than it is in your mind. Don’t forget that!
  5. How many other possibilities exist right now? The coaching conversation moves from limitation to possibility. Inside your company, what boundaries need to be pushed, what preconceptions need to be challenged, what policies need to be revised? Effective coaching points at possibility, not limitation.
  6. What does this look like, if we zoom out? See the big picture. What changes?
  7. What could make this easier? Hard is a habit, but it doesn’t have to be. A new approach the same old problems, without the same nagging difficulties, is at the heart of this coaching question. As Nelson Mandela said, “It seems impossible…until it’s done.”
  8. Who would you be without your story? Borrowing from the powerful coaching work of Byron Katie: we all create stories around our experience – and underneath those stories, we find out what’s really going on. Drop the story, and everything changes – if you are willing to see the possibilities.
  9. Who do you need to be in order to make this work? If you are doing the right things, when you are being an insensitive jerk, passive-aggressive imbecile or over-sharing idiot, guess what? It’s not working. Coaches know that how you show up is what creates the world around you. Notice the coaching shift here: focus on how people are showing up (”being”) and you can make some important discoveries around what they are doing.
  10. What needs to be done? This question is last for a reason. Have you taken time to address the personal roadblocks and mental stories that are robbing your team member (and maybe even yourself) of what needs to be done? Coaching focuses on internal motivation, not just instruction and direction. Moving directly to what needs to be done, before you consider the human being inside the action, is command and control – not coaching. To be fair, sometimes people need to be told what to do. But is that a sustainable strategy? Empower people to get out of their own way and take initiative – and your world will get a lot easier.

In The Great Game of Business, Jack Stack famously said, “People will support what they help to create.” Coaching offers an opportunity to co-create new results with your team members. The investment in coaching yields dividends in innovation – even for difficult employees. From time to time, we all tell ourselves stories that keep us stuck. We fall into a mind-trap where we believe that there’s no way forward – or that there’s only one way to win. The coach knows that possibilities always exist – and that the job is to find every way to win. From limitations to possibility: that’s the promise inside the coaching conversation. Find new possibility in your leadership – and discover how coaching can help you to reshape the future of work.

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