Coaching My Team Is Harder Than I Thought! (A Coach-the-Coach Conversation)

Become a better sales coach and sales manager today.

One of my subscribers emailed me with the following challenges and questions after reading one of my newsletters. Perhaps you have encountered similar challenges around being fully present and suspending your own agenda when trying to effectively transition from manager to coach in order to boost team performance. This is also a great example of coaching someone via email.

8-Steps to Creating a Coaching Culture by Keith Rosen1. The Leadership Transformation Needed to Authentically Develop a Team  (Valued Subscriber → Me)


First, thanks for your book, Coaching Salespeople into Sales Champions. It changed me into a developer of people, and letting my real personality/feelings/sense of purpose and responsibility really come alive in my job.

I recently asked each person on my team to prepare for our weekly call by asking this question of themselves:

“What is the ONE thing I can do such that by doing it, everything else will be easier/unnecessary?”

I was really excited to hear the answers. Luckily, I had read this week’s newsletter (12 Questions to Assess Your Coaching Effectiveness) so I was ready to sit back, listen, ask more probing questions, and allow my people to formulate more focused activity.

I got some great answers I was expecting/hoping for, but I also got some off-the-wall stuff that really didn’t fit into what I was looking for…maybe it showed me some people’s heads aren’t where they need to be….maybe it showed me that what they need is not what I think they need.

My question is: How do you confront someone when they give you an answer that isn’t in the same universe as what you were hoping/anticipating they would say?

Just as an example to clarify: I had one guy tell me the most important thing he could do was to wake up 30 minutes earlier and exercise. I kind of get that but I was thinking more work-related. I think I am showing how hard it is for me to suspend my own agenda here…..

Thanks for the all the help to date, and appreciate your consideration around helping me with this.

2. The Art of Being Present to Build Trust & Leverage People’s Strengths (Me → Valued Subscriber)

I am so appreciative of your kind words. However, what is most important to me is how these books have contributed to your success; which is the only reason why I continue to write and share my ideas with people like you. So, thank you for that acknowledgement and for the opportunity to contribute to you! Finally, it’s my pleasure to support you so that you can leverage your natural authentic self, strengths and gifts!

Now, regarding your question, it sounds like you already sense the correct answer is within you. However, let me add a little more strategy and methodology behind it to further support you and how you can coach someone around this situation to make an impact around his career. I’ve taken the liberty of copying and pasting three parts of your email below to ensure clarity and exactly what I am responding to.

I got some great answers I was expecting/hoping for, but I also got some off-the-wall stuff that really didn’t fit into what I was looking for…maybe it showed me some people’s heads aren’t where they need to be….maybe it showed me that what they need is not what I think they need.

Pause: The fact that you were expecting or hoping for certain answers sends up a red flag. I’m sensing there was a part of your own agenda and expectations showing up here. When it comes to coaching, and to life, an expectation that goes unfulfilled is a disappointment. (Just think about how you feel when you have certain expectations of others and they don’t meet your expectations.) But a possibility that goes unfulfilled is still a possibility, for you continually co-create new possibilities throughout a conversation that neither you or your direct report saw before.

Remember my definition of coaching. The Art of Creating Possibility. Not, “The act of instilling my expectations into the conversation and driving my own personal agenda.”

Now, to get more cerebral on you, think about the three points in time. The past, present and future. At what point in time do expectations live; your goals, your agenda, the end result or the outcome? In the future. Even if the future is 5 minutes from now, it’s still a point in time that has not happened yet.

However, at what point in time do possibilities live? Where does the coaching process live? Where does active listening happen and where does creativity occur? In the present. Why is this so critical? Because a possibility is created in the moment. It hasn’t been created, nor formulated when you start a conversation. You haven’t ‘already listened to’ the entire conversation in your mind, nor are you ‘already thinking’ about where to drive the conversation to where you want it to go.

In what point of time do you coach? In the moment; in the present. And what do you coach? You coach the process, not the result or your expectation/agenda. (If you haven’t read my recent blog, it may resonate for you. A Letter of Thanksgiving.)

So, to your observation:

…maybe it showed me some people’s heads aren’t where they need to be….maybe it showed me that what they need is not what I think they need…

This is accurate. And that’s okay! After all, the whole point of coaching is to uncover the new opportunities for talent development and that includes developing, furthering, advancing and refining both their skill set as well as their mindset.

So often, managers think they already know what their people’s developmental gaps are, simply by looking at the person’s activity, results and a spreadsheet. But if you’re not asking well crafted, open ended, non-loaded coaching questions or you’re not observing them, then you’re filling in the facts with assumptions or getting your data from a spreadsheet.

And you can’t manage from a spreadsheet. Data only tells you what is going on. It doesn’t tell you why; it doesn’t provide you with the root cause of certain beliefs, attitudes or behavior and it doesn’t provide insight into the quality of their activity and how effective and skilled they really are at performing a certain function, task, facilitating a conversation or their true selling acumen.

Most important, the beauty of coaching is to truly coach, respect and tap into people’s individuality; not to build robots or “mini-me’s.” So there’s a fine line between making sure people meet your business objectives and career expectations (sales targets, commitments, behavior, etc.) and judging them (“Well, when I was in their shoes, this is how I did it…” Or “This worked for me so this is what they should be doing.”)

Let’s explore your next question below.

My question is: How do you confront someone when they give you an answer that isn’t in the same universe as what you were hoping/anticipating they would say?

Building off my prior comments, it’s critical to suspend judgment and your agenda when coaching someone. And that doesn’t mean abandon your business objectives, sales targets or goals. What I’m referring to here, is parking your agenda during a conversation so that you can be fully present and engaged.

It’s not about them being right or wrong or good or bad. It’s about first, seeking to understand that person’s point of view. Once you do this; once you can truly understand and ‘get’ where they’re coming from and what their truths are, you are then in a position to deliver authentic, effective coaching and support.

In addition, doing so stimulates the law of reciprocity. That is, “If I value your opinion and respect your opinion, you’ll be open to respecting and hearing my opinion.” Conversely, once you pass judgment, or ‘make someone wrong’ or make them feel ‘less than’ or ‘stupid,’ or if you invalidate them in any way, you begin to erode trust and shut them down. Remember, in every conversation and in every interaction, you are either building trust or eroding it.

Now, that being said, what’s the tactical response that supports this methodology and way of thinking? Here it is; if we’re seeking to understand their point of view, then do so! Here’s what that can sound like during a conversation.

“Hmm, it’s interesting that you see it that way and I certainly respect your point of view. Can you share more about that to help me understand your opinion around this?”

Or, if someone provides you with a half-baked solution, or a solution that, as the sun will rise tomorrow, you know for an absolute fact their solution will not work, don’t shut down their ideas and start pushing yours. Instead, you can coach them around this so that they can, in turn, see their own Gaps. That could sound like, “I appreciate you sharing your opinion with me. How about we walk through your idea/strategy together through to completion to ensure it will achieve the results you really want.”

This second question allows them to self-assess their idea, strategy or solution through to completion and by doing so, they uncover their own gaps or gaps in their solution, strategy or approach. When this happens, real breakthroughs occur, instead of telling them, “you’re wrong” or “that would never work.”

Remember, what people hear, they resist. However, what people create and tell themselves, they believe.

In every conversation, to stimulate the law of reciprocity, create trust and deeper level of engagement, it’s critical to always first seek out and listen to the other person’s opinion and point of view. Now, that doesn’t mean you have to agree with it but you need to respect it because through their eyes, it’s their truth.

If you find yourself having a reaction to what someone is saying, it’s probably because you’re now passing judgment about what you perceive is the ‘right answer’ and as such, are trying to control the conversation. Here, you’re demonstrating a strong attachment to the outcome or solution you want. Now, you’re driving your own agenda, expectation and desired outcome. This isn’t coaching nor is it creating any new possibility or a better, collaborative outcome; it’s being directive.

Moreover, the law of reciprocity begins with you. Again, if you respect their point of view; in turn, they will respect yours and as such, be more open to your coaching and observations.  Here’s a blog I wrote that will also support you around creating new possibilities and provide you with some additional questions to facilitate a positive, engaging conversation, instead of shutting the conversation down. To Avoid Confrontation, Seek to Understand Their Point of View.

Just as an example to clarify: I had one guy tell me the most important thing he could do was to wake up 30 minutes earlier and exercise. I kind of get that but I was thinking more work-related. I think I am showing how hard it is for me to suspend my own agenda here…

Regarding your observation above, yes, your agenda is showing 😉 And why isn’t this work related? There’s a direct relationship between self-care and productivity in the workplace. Study after study supports this. I know from personal experience, the more time I take for myself, that is self-care, the more effective I am at work and at home. And self-care is personal. It can mean different things for each person. For me, it means spending a couple of hours almost every day working out in the gym, biking, golfing and playing guitar. For others, it could mean taking a walk, doing yoga, meditating, sitting outside, gardening or other hobbies, reading a book, or even downtime watching television.

Here are some questions that you can ask this person regarding this specific situation that would open up a new dialogue and create some alternative solutions, especially as it relates to their career:

  • “Wow, that’s great! So if you were able to wake up 30 minutes earlier and exercise, what would it mean to you?”
  • “How would this impact you both personally and professionally?”
  • “How would this have a direct effect on your productivity and performance at work?”
  • “What are some of the things that you would be able to do more of/better as a result of achieving this?”
  • “How would accomplishing this every morning make you feel when you come into the office?”
  • “What would be some measurable outcomes/results you would expect at work if you were able to achieve this personal goal (at home)?”
  • (Conversely) “If you aren’t able to do this, how would this impact you?”
  • “This sounds like it’s very important to you. So, what are some of the implications if you do not honor this personal goal?”

Not only do you want the person to connect this personal goal to their performance, productivity and satisfaction at work but you also want them to uncover and understand the implications and cost of not doing this and how it would impact them both personally and professionally.

Think of it this way. When you’re able to align each person’s personal goal with your business objectives, you now have tapped into the most powerful force that you as a leader can leverage. ALIGNMENT. Now, you have each person focused on a shared vision because you’ve aligned their personal and professional goals with the company’s objectives, so everyone is now focused on the same shared goal. In my book, Coaching Salespeople into Sales Champions, I discuss how managers can actually achieve this through a strategy that I call, the Art of Enrollment.

I hope this helps. And let me know how this works out for you! Wishing you continued success!

3. What about the WHY? (Valued Subscriber → Me)

Thanks for the response. Much appreciated. Here is a (possibly overly truncated) summary: Ask the question. Hear the answer. Seek to understand the WHY behind the answer. Create possibilities from the WHY to increase performance.

I love this from your email: “Remember, What people hear, they resist. However, what people create and tell themselves, they believe.”

4. Uncovering THEIR Gap – It’s Not about You (Me → Valued Subscriber)

One follow-up question, Keith. What if the WHY and the answer don’t affect the area of performance that needs to improve?

Then my friend, you’ve uncovered their Gap and the coaching opportunity. That is, what they can’t see on their own. And it’s at that point after you seek to understand and respect their opinion that you can fill in the gap with your observations. Managers get stuck around the order in which they do this during a conversation. They hear the problem, assume rather than assess the facts, then dump their ideas and answers.

Instead, looking at the summary of the coaching process that you shared in your prior response, now, your  you’re listening, assessing, seeking to understand their point of view, uncovering their Gaps, then sharing what they can’t see on their own or you’re asking the questions that stimulate self- reflection so that they, in turn, uncover their own Gap. The questions I’m referring to asking are similar to the questions that I provided you in my earlier response. That’s the true power of coaching.

Otherwise, if you hear what’s going on then start offering up solutions and things they can do, you run the risk of being redundant and telling people what they already know or have tried. At that point, you’re not giving value, and they’re no longer listening to you.

5. Light Bulb! (Valued Subscriber → Me)

Thanks so much. Light bulb moment! I never really grasped “The Gap” part of your book. Intellectually, I did, i.e. it made sense. But, now, I really get it!

This stuff is like that 100th push-up. You power through the first 99, but that last one takes every bit of energy, willpower and grunting you can muster…but, it feels so good when it is over…and without it, it feels like you missed the point of the first 99. This stuff is hard!

6. Becoming Unstoppable! (Me → Valued Subscriber)

Sometimes we need to hear a certain message a few different times, said a few different ways and also be at a point where we are actually ready to receive it!

Coaching; really good coaching, is only difficult in the beginning because it’s new. For example, if you’re right-handed, it’s like tying your right hand behind your back and now, you have to write with your left hand. And if coaching was so easy, then every manager on the planet would be a world class coach!

This takes a conscious effort to change how we think and how we engage with people. It requires breaking old habits, both in how we do things, as well as our thinking around what it means to be a great leader, thus changing the dynamic of our interactions and conversations. The payback is, the impact you make and the outcomes you achieve are worth every second. Just like that 100th push up! When you finally do 100 push-ups for the first time, the second time you do so, it’s a lot easier.

It’s the same with delivering great coaching! First, the idea and steps of delivering effective coaching are in our head. That is, you’re thinking about the steps, the right questions to ask, and suspending your agenda. Eventually, you do what the best coaches do, which is, shift from coaching from your head to coaching from your heart. That’s when you make coaching your own, leveraging your own style and personality and when you’ve made the final transformation to being the best leader you can be.

So, build up your stamina and you’ll be unstoppable!

Photo Credit: Auremar (via Shutterstock)