5 Coaching Strategies of Top Bosses

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Coaching is a severely underutilized leadership skill and many leaders overestimate the quality of their coaching capabilities because they rarely get feedback on their coaching skills. 

Why is coaching so beneficial? To simplify it, coaching is extremely beneficial for the two following reasons: (1) it is very engaging and motivating for others – coaching develops & engages your high-potentials; (2) it creates self-accountability, the more you coach someone, the more that person reflects on their own and starts to do their own post-mortem analysis of their successes and failures, which informs their future efforts. People who are coached are far more invested in the success of their efforts. 

Many leaders prefer to give directions most of the time because coaching requires lots of up-front time and patience. Being directive is time-saving in the short-term, but has no long-term benefit. Coaching takes time in the short-term and yields many long-term benefits; the investment of time now will actually save you time in the long-run. Not every conversation needs to be a coaching one; you must be intentional and use your best judgment about when it’s more important to be directive and share your domain expertise versus coach for increased improvement of performance and capability. 

Here are 5 foundational coaching strategies that top bosses implement

1) Exhibit no judgment

Top bosses create a safe space for the coachee to be open and exhibit vulnerability; they don’t take things personally because they recognize this isn’t about them. They maintain an open-mindset and exhibit no judgment. If people find you closed-minded or judgmental, they won’t open up with you. Additionally, they need to trust that you will keep what they say confidential. 

2) Believe in the person’s capability and they are wholly resourceful

Top bosses acting as a coach come from a place of positive intent. They believe that the coachee is capable, resourceful, and a fully functioning human who is able and capable to solve their own problems and self-correct when necessary. Question yourself: do you truly believe this? Can you operate from a place of positive intent? If you don’t, you need to work on yourself before you try to coach others. 

3) Ask open-ended questions

Top bosses acting as a coach ask open-ended, non-leading questions and they prompt for more information to dive deeper. Examples are: 

❓ What are you hoping to get out of our conversation today?

❓ Tell me more about that. 

❓ What would you like to see from that person? 

❓ What are you thinking about doing? 

❓ How are you going to do that? 

❓ What do you make of that? 

❓ What meaning are you assigning to that? 

❓ What’s coming up for you? 

❓ What’s getting in your way? 

A common trap is when leaders ask leading questions, where they have a desired outcome in mind and are trying to lead the coachee toward their desired outcome/answer/solution. Top bosses don’t do this – when they coach, they don’t make it about them and their desired outcome, they attempt to learn and understand where the coachee is coming from. When a top boss uses this strategy in coaching, they might say something like “My thought here is X. What do you think?” and if/when the coachee disagrees with their thought or indicates that it doesn’t resonate, the top boss doesn’t take it personally because they aren’t attached to the outcome. 

4) Validate and empathize

Top bosses acting as a coach help others feel heard and valued. This is an extremely powerful and underused strategy. Far too often, leaders (and humans) want to dish out advice and help people solve their problems, without providing space to empathize, acknowledge, and help the person feel heard and valued. Top bosses acknowledge the person’s courage, beliefs, desires, passions, vulnerability and strengths and they genuinely empathize when appropriate. Examples are:

❓ I see your strength of teamwork shining through here. 

❓ That sounds challenging. Thank you for sharing this.

For more information, see my post Stop Invalidating Others At Work

5) Expand the coachee’s perspective

Top bosses acting as a coach help the coachee expand their perspective – about themselves, about their perception, and about the situation/problem/issue. Examples are: 

❓ What role are you playing in this?

❓ How are you in your own way? 

❓ What’s going to help you most in making this decision? 

❓ What haven’t you thought of yet? 

❓ How do you want to walk away from this situation? 

❓ What could you try that you haven’t tried yet?

Top bosses who take a coaching stance talk much less than the coachee during the conversation. Like anything, coaching is a skill that must be practiced to learn; you have to start somewhere. Since most leaders overestimate their coaching capabilities due to lack of feedback, try soliciting feedback on your coaching skills. You might want to go into a coaching conversation by letting the person know that you’re going to try a different approach and then ask them how it was for them. Good luck and keep me posted on your efforts! 

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