6 Final Questions to Assess Your Leadership, Coaching Skills and Impact – Part 3

If you’ve read Part One, and Part Two, this is the final installment of this three part series. Here are six more questions to help you self-assess, reflect upon and guide you on your continued transformation into a world class leader, and salesperson.

Managers, Learn How to Coach and Manage a Remote Team and Win More Sales. Online Course.

Here’s Part One and Part Two of this series.

1. How did you build trust and position coaching with your team?

Did you build the trust and transparency needed for coaching to be successful by setting positive intentions and aligning their goals with the business objectives?

Do your people trust you? How do you know? If you’ve ever felt, “I feel like my direct reports are just telling me what they think I want to hear,” it’s time to reassess and rebuild trust, reset your expectations as a manager, and clarify your positive intentions around your coaching efforts, and what’s in it for them. Here’s what that conversation can sound like.

“What I want for you is to experience the level of fulfillment and success that you want in your career. I’ve been working on my coaching skills so that I can best support you in achieve your goals. 

That’s why I wanted to talk about your perception of coaching is and your experience being coached, if at all. Then, we can create alignment around what great coaching is, set some expectations and parameters around our coaching, and what I can do to make this the most valuable experience for you.

Are you open to discussing this to ensure we make it work for you?”

Then, you can continue with some of these nonnegotiable questions to help clarify your intentions and align expectations when beginning a coaching relationship.

  • How would you define coaching?
  • Have you ever been coached before? What was your experience like?
  • If you could (re)define the parameters and definition of coaching so that it’s a valuable experience  for you, what would it be?
  • What would your expectations be of me from our coaching?
  • What concerns, if any, do you have about our coaching and what we discuss?

While your intentions may be pure and you are truly coming from the right place of wanting to support you team, if they don’t know what you are intentions are when asking all of these questions, why you are doing it and what’s in it for them, like any human being, their default file is fear.

The result? Resistance and push-back around being coached or managed virtually, especially from your top performers or seasoned veterans, is imminent. Now, compound that with people who have never worked remotely before. This requires not only a different communication platform, but an evolved communication strategy.

Toxic Coaching Tactic: When expectations aren’t clear, people default to fear.

Managers must take the time to set expectations and help their people develop the structure to create a productive, virtual workplace in a way that honors how each person wants to be communicated to, coached and supported, as well as how they can best manage their day.

2. How has coaching been positioned within your organization?

Building off number one;

  • Did you and your company position coaching as a perk, an incentive, an option, an obligation, or a remedial response to underperformance?
  • Are you only coaching people when there’s a problem or when dealing with performance issues?
  • Do your salespeople view coaching as a gift and as a way for them to continually better their best or do they look at coaching as more of an obligation to “appease their manager” or worse, a punishment?
  • Has your coaching ever been met with resistance? Do you, as a manager, feel that you can’t call it “coaching” because the word coaching, as result of poor coaching, has been branded a dirty word?
  • Do you/does your team view coaching as the critical skill every world-class leader must develop in order to build champions? Conversely, is it viewed as the “Flavor of the Month” that your company is pushing on you, knowing that this initiative will die out soon like the others?

Without resetting the parameters and foundation around what great coaching looks and feels like and the results you can expect, when you’re only coaching when there are problems (all day long) or dealing with underperformers, then you’ve just positioned coaching as remedial, and only for the underperformer.

Then, managers wonder why their solid B and A players never want to be coached!

Coaching must be positioned in a way that would empower people to want to be coached. That includes getting managers excited about coaching and ensuring everyone is getting coached, while enjoying the value!

Now, if you happen to be the recipient of poorly positioned coaching, here is your moment; your opportunity to coach up! If you need some tips and templates on how to do so, download my ebook, Coach Up!

Great coaching starts with an authentic non-negotiable commitment to your people. So, if you really want to make your people the priority, then make coaching your priority.

3. Are you carving out one hour each week for peer to peer coaching?

Sure, every manager needs to coach their team. However, who is your coach?

The manager is responsible for creating the culture among their team. And that means exemplifying what great leadership looks like. This includes being the poster-child for coachability!

Be intentional about scheduling consistent, one to one or team coaching with your peers, aside from working with an external coach, if you choose to.

While coaching your team is a non-negotiable, so is peer to peer coaching. After all, if you want to build a world class team, then change starts with you. That means making peer coaching your priority.

Have someone neutral (sales enablement, a senior leader, someone in learning and development, HR, etc.) pair people up with different peers throughout the year, even ones in different departments.

Before you make the assumption that every manager must be teamed up with someone in their department, challenge this line of thinking. After all, what’s the root cause of departmental silos?

A lack of TRUST and the assumptions made about other people, their roles, and other departments. If you want to eradicate departmental silos, take the time to understand each person’s position, points of view, challenges, and how you can best collaborate together.

In addition, while managers may feel, “But I don’t know their job,” consider this. It’s actually easier to coach people who you don’t know much about, because all you have is the question, rather than the temptation of shooting out answers, if you’ve either walked in their shoes or share a similar role.

This is the only way to truly break down departmental barriers and silos and rebuild trust, while developing the future leaders of the organization.

Besides, if you’re not growing, being coached, held accountable, are practicing your coaching skills, and are open to feedback by the people and departments you rely on to get your job done, how can you expect your team to?

Most important, without consistent peer to peer coaching, it will be very difficult, even impossible, to build, adopt and sustain a healthy coaching culture.

Tip from The Coach. If you don’t have the appointment, you don’t have the commitment. Schedule Peer to Peer Coaching. Just like your employees need someone in their corner supporting them unconditionally, so do you.

4. How good are you at living in the present moment?

You can’t be a great manager without mastering the skills of coaching, and, more important, the inner game of coaching and leadership. The ability to live in the present moment. Technology has made it practically impossible to live in the moment more than we do, as we’re constantly being pulled in different directions, with competing with conflicting goals and ever-changing priorities.

What if I told you that 95% of your time, (and I’m being generous) you’re either living in the past, or in the future?

That is, you’re either focusing on what’s happened in your life and the decisions you’ve made, both good and bad, mostly the ones you regret, or like most people, you’re focused on the future expectations, goals and the results you need, want and expect in business and at home.

The sad cost is, this comes at the expense of the present, which is where your life happens. Where the daily miracles of life occur; whether at work, wit your team, customers, home with your family, and especially with your children.

In addition, when focusing on a future expectation or result, you’re surrendering your personal power, allowing external results and experiences to determine your mindset, confidence, self worth, and internal state.

Every company’s culture, whether admittedly or not, is sales quota, scorecard, K.P.I., metrics and result driven, and every person has a target on their back to achieve results.

The costly result of this culture is, most of the time, you’re living in the future, focusing on what’s next, rather than what’s now.

Here’s the conundrum. My definition of coaching (and selling) is, “The art of creating new possibilities.”

Active listening, creating possibilities, mindfulness, connection, engagement, selling, innovation, collaboration, creativity, communication and executing a process to achieve greater results, all happen in the present. (I.e. Coaching)

So, if you’re not present, you can’t sell or coach masterfully.

Living in the future is both an occupational and a lifelong health hazard. With all of the competing priorities and changing responsibilities coming at us from work and home, it takes conscious effort to live in the moment.

So here’s a duality. You don’t have to choose one or the other. What if you can have both! That’s the power of creating new possibilities. So try this on.

Be mindful of the future. While living in the moment.

Besides, your goals aren’t going anywhere. They’re set. However, your life happens now. Be present.

5.  Have you assessed every person’s coachability index in terms of their engagement and commitment around coaching?

I’ll keep this one simple. There’s only one factor that determines whether someone is coachable; one characteristic that needs to be present.

That is, a DESIRE to change for the better.

While this level of desire to change or improve may vary from person to person, it’s the manager’s responsibility to uncover their coaching sweet spot, so you can ensure the coaching is aligned with who they are and what they want.

6. Do you feel that your value as a manager is being the subject matter expert?

Sure, it’s certainly part of your value but that’s only going to take you and your team so far.

To compound this conundrum, I’ve had countless managers tell me the reason why they were hired was because they were the subject matter expert and a great problem solver!

In truth, to build a top performing, collaborative, trusting team, managers must honor their primary objective. That is:

Making your people more valuable every day.

The byproduct? A top performing coaching culture of champions will emerge, that will always withstand the test of time.


What are your thoughts? I’d love to hear your comments. Any questions, feel free to reach out and connect anytime, as I want to be a resource for you. I’ve also opened up my personal one on one coaching practice for those who need it most during these challenging times.