Coaching Up for Alignment – How To Use Coaching Skills To Improve Workplace Dynamics


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By: Corry Robertson, PCC

coworkers sitting at desk discussing project

There are many ways for employees to communicate better with the leaders at their company, but one of the best ways to do this is to use a skill called “coaching up”.

When we think of coaching we normally think of it as something that leaders do to support and develop their employees, but what most people don’t realize is that the coaching conversation can be initiated by an employee to better communicate with their manager and get clarity on deliverables, priorities, and performance expectations.

Does the idea of coaching up pique your curiosity?

For those of you who take part in conversations with the business owner, executives at your firm, your direct boss, or other leaders at your company, I’ve prepared a mini coach training for you. 

Don’t manage up, coach up instead!

A Coaching Up Story

Johnathon is a great guy and means well but he’s under a lot of extra pressure and is on the brink of exhaustion these days, as is everyone.

Because he’s so overextended all of his direct reports have noticed that Johnathon’s delegation and follow-up style are inconsistent and it’s not always clear what Jonathon’s priorities are or what he wants as deliverables. He’s just trying to hold it all together during very difficult times.

His team wants to step up and do their share but…

Johnathon is also short-tempered these days and with this short fuse, he has a hard time hiding his irritation when mistakes happen or when things are done in a way that wasn’t what he wanted. When he gets like this, he’s likely to snap at people and blurt out some pretty harsh criticism and even the occasional threat!

No one wants to make mistakes and no one wants to be embarrassed in front of the rest of the team or be put on a PIP (personal improvement plan).

Johnathon is not making it easy for his team.

Roberta for one is trying to keep her head down, do her work, and stay out of Johnathon’s way!

Roberta is smart, dedicated, and perfectly capable of doing great work but under these extra stressful times, she is making unnecessary, embarrassing mistakes and having to answer for them. 

This makes her self-conscious, causes her extra stress, with more exhaustion and more mistakes – a downward perpetuating cycle. This climate has a lack of trust and psychological safety. It is starting to debilitate Roberta and many others at the company. 

After all, they have worries outside of work too.

What can she do to make sure that she directs her time and energy into the right things, the right way? How can she support Johnathon to the best of her abilities? After all, she wants to!

coaching up meeting

The Coaching Up Process

I can’t give you an entire training on leadership and executive coaching in a blog post but I can give you a powerful thought process to think about.

Let’s point out the coaching process as this story unfolds:

Imagine a conversation is taking place between Johnathon and Roberta. Johnathon is delegating a project to Roberta.

“Roberta, I want you to brief The Waterfall Team on the status of our change management strategy rollout. We have a call with them on May 18, 1:00pm. That gives us two weeks to prepare.”

Johnathon then goes on to describe the mandate. He talks for several minutes while Roberta is on the edge of her seat, afraid she’s going to miss important details so she’s taking notes.

Coaching Up Tip #1

When you’re trying to write down everything someone is saying, you are not fully listening or observing. I always tell my coaching students and mentees that if you’re taking notes, you’re not listening.  

Especially in a situation with your boss, leader, or manager – it’s important to be fully present and listening.

“Any questions?” he asks but the question had a tone that could be perceived as a statement meant to close the conversation as if the question mark was a period.

Johnathon is busy with many competing priorities and now that Roberta is fully briefed, he has to move on.

“Yes, I do have some questions,” Roberta says with confidence.

She knows that extending the meeting to get clarity will extend the meeting time but with well-chosen questions, she’ll save them both time in the long run by avoiding misunderstandings that lead to having to go back and do things over. 

Do-overs, correcting mistakes, and recovering from the ensuing tension and conflict are the time-wasters, not the coaching conversations.

“Sure. What are your questions?” Jonathan replies. Roberta can feel the impatience brewing in her boss.

Coaching Up Tip #2

Here is Roberta’s opportunity to leverage coaching as a communication style by asking clarifying questions such as these:

First of all, check to make sure you understand the WHAT of the project by paraphrasing:

“I understand that you want me to brief The Waterfall Team on the status of our change management strategy rollout and the call is in two weeks from now, May 18, 1:00pm.”

Secondly, get to the WHY of the project by expanding the gap between where you are now, what Johnathon wants you to achieve and what success looks like to him:

“What is the main objective of the briefing meeting?”

“What are the key takeaways that you want Waterfall to walk out with?”

“What will make this a successful meeting for you?”

Coaching Up Tip #3

When using the coaching approach with a leader or executive in this way, it leads to exploring assumptions and blind spots that cause misalignment.

Remember, Johnathon believed he told Roberta everything that there was to know and that what he told her adequately set her up for success.

This is a natural belief to have but the magic is in remaining mindful that we don’t live in each other’s heads.

The executive’s mind is often managing many different topics and switching between them at an extremely fast pace so it’s important to hold discovery conversations in this way to allow for focus on the topic at hand for long enough to achieve alignment around expectations and desired outcomes.

Roberta asks these questions to clarify the assignment and achieve alignment. Now Roberta knows WHAT she is assigned to do, and she knows the WHY she is doing it.

Coaching Up Tip #4

The next step in using coaching skills during this conversation is exploring HOW so now it’s time for questions like:

“The last time we presented to Waterfall, we had a slide deck. Do you want a new deck or should we build off the last one?”

“Are there key issues or grievances that need to be addressed? I will prepare responses in advance”

“How much time do I have to present?”

“Will I be the sole presenter? (if not, who else needs air time?)”

Coaching Up Tip #5

You will notice that Roberta has not brought up any potential obstacles or barriers in the way of getting this assignment done.


In the coaching conversation model, addressing obstacles and barriers comes intentionally later in the conversation for many important reasons.

For example, until clarity is achieved, you don’t know what the obstacles and barriers are so it’s a waste of time to discuss them yet.

Often while discussing the WHAT, WHY, and HOW of a project, the perceived obstacles work themselves out because there are factors that you didn’t know about, or your concerns were addressed organically.

Now Roberta is ready to discuss those obstacles and barriers. That could look something like this:

“Johnathon, based on the last briefing of this scope that I gave, I anticipate this project will need half a day of my time. To carve that out, I will need to de-prioritize Forest Grove Project, Riverbed, or Starry Night. Which one can move? Riverbed is in good shape based on the timeline. That would be my suggestion.”


“Johnathon, the design team has had a lot of turnover lately. They are training someone new but they are still short-handed. I’m not sure they can push out a new deck in time. My suggestion would be to outsource this one but I will need your sign-off on that right away so that we can get going”.

Coaching Up Tip #6

Managing Progress and Accountability

They’re almost done with their conversation so the next thing is to make sure that they are aligned on the commitments that they are holding themselves accountable to.

“This is great Johnathon. Just a few more questions:

I’m pretty excited about this project and I’m confident that I can do a good job.

I’d like to book some time with you next week just to make sure that the presentation is aligning with your expectations. That will give me enough time to course-correct if needed. How about next Tuesday at 9:30?”

So there you have it! 

Roberta got the clarity and direction that she needed from her executive by using her coaching skills. She knows what the project is, why it’s relevant, how she’s expected to achieve it, and by when.

people high fiving in group

Why Does Coaching Up Work So Well?

Usually, we expect the more senior person to be asking the questions but the beauty of a coaching culture is that executives, managers, and individual contributors alike all have the right mindset and communication skills needed to take part in powerful, productive, conversations. 

These conversations allow everyone to think through the muddiness in their own minds, explain clearly, and ask the kind of powerful questions that lead to raised awareness.

Whenever I get the chance to say it, I wholeheartedly declare that coaching is a leadership skill in action.

On The Job Coaching Skills

If you take a closer look at the conversation above you’ll notice that it not only covers the skills of co-creation, active listening, and asking powerful questions, it’s also a conversation about SMART goal setting, delegation, workload management, and performance management.

Coaching skills help in all aspects of on-the-job management. I know many people love to help others and so are drawn to coach training with the dream of someday starting their private practice, but you don’t have to quit your job to practice as a coach!

You can be a powerful source of good right where you are by coaching on the job.

For those of you who want to know about coaching in the workplace and coaching up, hopefully this mini-lesson helped empower you with some ideas on how to ask your manager for more clarity so that you can deliver the kind of results your boss is expecting from you.

For those of you who have people reporting to you, I hope this overview reminds you that your people want to do a good job and make you happy. They want to carry their share of the load so help them help you by being approachable and coachable.


Coaching and being coachable is a unique skill set that is 100% learnable. Coach training teaches you how to recognize the potential in a person and then help them transform that potential to performance – but the great thing is you can use these skills no matter where you are at on your career path.

Once people understand how coaching works and why it’s so beneficial for an aligned workplace environment, they are usually really excited to practice and bring their skills to work by coaching their colleagues.

Are you interested in bringing coaching into your company in a real and meaningful way, whether that’s for your own skill set, or to develop a coaching culture within your organization? 

Book a discovery call with me and let’s explore how you can do just that!


Did you enjoy this article?  You might also like:
How to become a certified coach:  Understanding ICF Credentials and Certification Programs
A model for effective SMART goal setting for team leaders, the C3 Principle 
The surprising problem with coaching for HR Professionals


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Corry Robertson

Sought-after coaching culture expert, Corry Robertson has been helping leaders uplevel employee retention and performance for over 20 years.

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