Coach Up! (Part 3) – 8 Guiding Principles When Coaching Your Boss

Become a better sales coach and sales manager today.

In addition to managing your mindset, disposition, and communication strategy when coaching up, these eight principles will ensure your coaching efforts are both well received and effective.

(Here you can find the first two articles in the Coach Up Series: Part 1 and Part 2)

1. Passive Coaching Isn’t Coaching

A passive approach to coaching up will not always be that effective. Sending an email or leaving an article or a book on your boss’s desk about how to coach, communicate or manage a team isn’t my idea of coaching up. While this strategy could be marginally effective, how this is received depends upon the relationship you have with your boss. Your well intended efforts could also blow up in your face if your intentions were not clear and as such, misinterpreted by your boss.

2. Confirm They are Ready to Listen

When approaching your boss about a conversation you want to have with them, confirm that they are not only willing but are also ready and in the right frame of mind to have that conversation. Trying to coach up while they’re in the middle of handling a crisis, right after they hear some bad news or have a less than favorable forecast meeting is probably not the best time. Take their pulse on the timing before jumping into the conversation. It would probably be more effective to schedule a time on both of your calendars to have this conversation to ensure that the proper amount of time is allocated for this important discussion.

3. Share The Benefit They Will Realize

To make a positive impact, your initial approach has to be focused on the value that your boss would realize. What is in it for them, why should they listen and entertain your request in the first place? While it’s clear that you’re having this conversation to create a better opportunity for yourself, how you position the conversation is critical. As such, approach this discussion not solely focused on you and what you want but about the greater goal or meaningful result and the value that your boss, even your company would experience. If you were looking at your agenda through your boss’s eyes, what would be something they would find worthwhile to achieve?

4. Positive Positioning is Key

Focus on the pleasure, the goal or the end result rather than dwelling on the problem. Managers get tired of hearing about problems or what is wrong and they hear these things throughout their entire day from multiple sources; their customers, employees, venders, even their boss. In fact, most of the time, when approached by their direct reports, managers are already expecting to hear about some issue or challenge that needs resolution. So, first and foremost, be positive so that you can focus on the positive result. In turn, this will help shift your manager’s listening, making them more open, receptive and willing to have the conversation with you in the first place.

5. Honor the Two Conflicting Truths

Remember, you’re coaching to a certain degree, which means embracing the most challenging part of coaching. That is, balancing out your objective in the conversation while surrendering your agenda and having no attachment to the outcome at the same time. Yes, two conflicting truths that co-exist simultaneously. Besides, while you’re approaching the conversation to generate an expected outcome, there may be a better solution co-created within the conversation that you never even considered before. Sure, you have an agenda, however, it is during the actual conversation that you want to keep your mind open to creating new possibilities and stay detached from your own myopic, preconceived solution or anticipated result.

6. Balance Being Obsequious with Being Pleasantly Assertive

Strategically positioning a positive conversation as it relates to the message you deliver is one thing. How you show up to the conversation is something entirely different. While you want to stay away from sounding like someone who is overly submissive, subservient or the proverbial brown nose, the pendulum can also swing to the extreme the other way. So, be mindful of your disposition going into the conversation. That is, find the balance between coming across confident and assertive while being respectful and humble. In addition, being an optimistic, encouraging person goes a long way in facilitating a deeper, more meaningful interaction with someone. Besides, what boss really enjoys being around a wallflower or a pessimist?

7. Keep The Past or The “Already Thinking” At Bay

If you’re already going into the conversation with a less than desirable expectation, such as anticipating an unreceptive reaction from your boss or a negative outcome, there’s a good chance that’s exactly what you’re going to get. There’s a symbiotic relationship between the way we think, listen and the questions we ask. For example, if you’re already thinking from a negative place, then by default, it’s going to affect how you listen. Now, you’re listening from that certain place or through a filter. Consequently, chances are you are not going to ask certain questions that can create new opportunities. After all, if you keep listening from the past and reacting based on a past experience or a future expectation, you will continue to create the same results as before. Expect the unexpected and be more of a ‘possibility creator.’

8. Ensure Forward Momentum

Make certain that the outcome of your conversation includes actionable next steps assigned to each person involved, along with a measurable timeline on each to ensure continued momentum that will result in the changes you’re looking for.

Photo Credit: Nick-K (Nikos Koutoulas)