4 More Indispensable Questions to Assess Your Leadership Coaching Skills and Impact – Part 2

If you’ve read Part One, you’ve probably noticed several opportunities to improve your leadership, remote coaching and management skills, to become the exceptional leader you can be. Here’s an additional four questions to self-assess, reflect upon and help guide you on your continued transformation into a world class leader, and salesperson.

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Here are four additional, indispensable questions to assess your management and coaching skills and impact. After reviewing these questions below, you’ll also find that these four questions apply directly to salespeople, as well. (Here’s the link to part one.)

Keep in mind, this list was curated based on working with thousands of managers throughout the world who all struggle with these same challenges. Please understand. I’m not saying this to invalidate you. Instead, to validate the fact that as you read through these questions, know that you’re not alone!

1. Do you act as the Chief Problem Solver, providing the solutions for your people every time they come to you with a problem or for the answer?

If you feel compelled to jump in and solve almost every problem people bring to you, especially during challenging and uncertain times, you’ve now become the very thing you want to avoid that will erode and sabotage your coaching efforts, accountability, and learning mindset you want to create among your team. The Chief Problem Solver. Moreover, you’re missing countless coaching opportunities, since you’re focused on solving the problem, rather than helping others do it for themselves by leading with coaching questions not answers.

If you have time to give an answer, then you have time to ask a question. So coach, don’t tell.

What does every manager want? A team of independent, accountable salespeople. What do you create when you take on doing other people’s job? The very thing you want to avoid; a team of people who are now dependent on you.

Even worse, if your solution doesn’t work, then it’s your fault and they get to blame you! Now, you’ve adopted their problem and made it your own, making yourself accountable for the solution, not them.

Coaching Conundrum – You Can’t Scale DEPENDENCY

2. Do you struggle to find topics to discuss during a scheduled coaching session or to get your people to open up?

If so, then you’re either pushing your own agenda, not proactively and intentionally observing them, you haven’t clearly set intentions and a safe place for coaching to occur, which created a trust issue, or the coachee isn’t planning for the coaching session.

The solution? Develop a Coaching Pre-Call Prep Form. Here’s the one I’ve developed that you can download immediately. This provides the coachee with the space and time to set clear expectations of every coaching session and the value they expect. Now, objectives can be achieved, and the coach can’t be made wrong if the topics discussed weren’t valuable to the coachee!

In addition, the coaching prep form also acts as a path to progress. That is, you now have the ability to look back and see how much each person has accomplished throughout the time you’ve been coaching them. After all, we’re all really good at reflecting and focusing on all the things we didn’t do or the problems we didn’t solve. We’re not very good at recognizing the wins, personal growth and the challenges that no longer exist because of the work you did.

3. How consistent are you with observation (joint sales calls, phone calls, field visits, peer interaction and collaboration, written communication, etc.)?

Are you observing your employees consistently in order to provide accurate feedback in a way that facilitates a positive and long term behavioral change?

If you’re not observing your people, then you don’t know what they’re really doing, which makes it difficult, if not impossible, to uncover what may be causing a dip or improvement, in attitude or performance, as well as additional coaching opportunities, especially with your top performers.

Consequently, you replace the facts with your own costly assumptions and share your ideas and solutions accordingly. Then, you wonder why you’re having repetitive conversations. It’s not because they’re, “Not getting it, even though you’ve said it 100 times.”

It’s because you’re making assumptions of the facts, and treating symptoms, rather than taking the time to get to the Why, the Gap or the root cause, which often can only be uncovered by first, having an alignment conversation with your team around the value of consistent, effective, and intentional observation and feedback and letting them know you want them to support you in the same way as well! That’s the law of reciprocity. The trust builder. And it always starts with you.

Remote Coaching Also Includes Remote Observation

In addition, you actually do have the opportunity to observe your team ‘in the field.’ Granted, your direct report may not be physically next to you when they’re delivering a presentation, during a coaching session or in a meeting but you can schedule a conference call with the salesperson and listen or even observe via video conferencing, a virtual desk-side observation, while that person works through their day, makes follow up calls to prospects or customers or when they’re cold calling, should cold calling be part of that person’s responsibility.

And even though you’re not physically present, you can observe other things as well that go beyond simply what you’re hearing.

For example, whether you’ve scheduled a time for a coaching session or a time to observe them over the telephone or video conference, are they prepared for their meeting with you? Are they efficient and organized? Do they have their notes, call list, objectives and expectations clearly mapped out? Are they focused or distracted?

From the Sidelines: Why is intentional, consistent observation and coaching essential to your teams success? Because people cannot change what they do not see.

That’s why the sport coach stands on the sidelines, observing what their players can’t see themselves. After all, even the top athletes in the world can’t self-diagnose when they’re in the middle of a game and neither can your salespeople. In either case, they’re playing to win. And if you’re struggling to find coaching opportunities with your top performers, simply take the time observe them. You’ll find many opportunities to further develop even your most talented performers.

4. Are You Coaching the MESSAGE?

Leadership like selling, is a language. And the language of leadership and selling, is coaching. Since selling is simply a language, top performers communicate more powerfully than lower performers. They listen at a deeper level and certainly ask the ‘tougher,’ more precision-based supportively challenging questions that get to the core of that person’s known and unknown needs, concerns, buying process and priorities.

As the manager, this is your chance to not only uncover more coaching moments and developmental opportunities but to assess best practices around the behavior you want all of your people to engage in, including what is said, how it is said and what is better off left unsaid.

Since your direct reports are also interacting via email with their prospects and customers, reviewing their written email and the message they’re sending in written form will provide you with invaluable insight and uncover many opportunities for continued improvement and growth.

Remember, when cold calling, prospecting, and sending messages via text, email or via social media, until that prospect becomes a customer, YOU and your messaging are the product and what you and your company are immediately evaluated on.

And if you’re a global manager, where some of your direct reports are calling on companies in certain regions of the world where you may not speak their language, do not despair! You can still observe them! What can you observe? Well, you can observe their tone, pace and voice inflection. You can observe whether or not they’re cutting the customer off when speaking with them. You can also observe if they are talking too much or if they are asking more questions and listening instead of talking. And you can also have your peers who speak that language do some mutually agreed upon observation of your direct reports.


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.