Top coaching skills managers need to lead successfully

Every expert used to be a beginner. Despite a few stories of prodigies and savants, the rest of us are condemned to travel the long, bumpy road of experience. If we’re lucky though, a good coach is there to provide us with encouragement and guidance along the way, helping us reach our objectives.

Good mentoring can play a significant role in helping people grow the confidence needed to take chances, develop leadership skills, and build valuable workplace relationships. One professional coaching survey reported over 95% of coaching clients said they would willingly repeat their coaching experience. Why is this?

When coaching is effective, people feel better about their job because they identify with their role and even take pride in it.

The original coaching model

Turns out influencers weren’t the first ones to offer 6-week courses on perfecting the work-life balance. Among the first modern executive coaching approaches was Sir John Whitmore’s GROW model, published in his 1988 book Coaching for Performance, where he lays out how to set goals using the GROW framework:

  • Goals: goals and aspirations.
  • Reality: current situation, internal and external obstacles.
  • Options: possibilities, strengths, and resources.
  • Way forward: actions and accountability.

Like all mnemonics, the GROW model has its flaws. None of the points lay out how to initiate a coaching conversation. Goal setting, a highly subjective and individual process, can take more time than people expect. The model also doesn’t involve much psychology and can gloss over the complexities that led to coaching in the first place.

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For all its imperfections though, Sir Whitmore’s coaching model offers a foundation that influences coaching culture today. Let’s have a look at the GROW model.

Establishing realistic, achievable goals

There’s a saying that if you judge an elephant by its ability to fly, it’ll live its whole life thinking it’s a failure. This is true of people who need coaching as well.

Expectations should be clearly laid out during hiring, but when coaching is needed for improvement, there needs to be some compassion. Everybody wants to do well at work, and when it’s clearly not happening, delicacy from managers is required.

Start small—if an employee isn’t meeting your company’s standards, set goals that help them increase their output little by little. This isn’t a performance improvement plan, just a way to improve their skill set and start getting more done.

For example, set a goal for how much work to get done before lunch. Time-bound, measurable goals establish a pace, which helps to build trust and give them confidence in the competencies they do have.

Small, achievable goals are important for people who aren’t meeting company standards. More than likely, these employees are already feeling the heat of not doing as well as they ought to, and firing off disciplinary language for their failure to do so isn’t likely to inspire them to do much better. Try to understand them before talking about expectations.

Put yourself in their shoes

The R in Whitmore’s GROW model stands for reality, meaning the part where managers discuss what’s preventing someone from achieving what they’re supposed to achieve. For managers, this is an important time to ask questions and practice active listening.

Does the employee feel too stressed out to perform? Are they distracted? Are organizational roadblocks getting in the way of productivity? Most importantly, have they actually been trained on exactly what to do to meet expectations? These are all important for clearing the way and helping employees keep up their momentum and succeed.

Mentorship plays a big role here—effective leaders offer stories about what it looks like to start at the beginning and develop proficiency, providing a roadmap for employees to plot their own course.

If you have empathy, now is the time to use it. Through powerful questions, you can understand where they are coming from and help them reach the next level of their career.

Charting a path forward

With expectations established and a frank conversation had about why, the next step of the coaching process is using resources and reaching milestones. For managers who prefer instant results to patience, this part can be challenging.

Be specific and offer constructive feedback. Talk about what will work versus what won’t. For example, if a team member spends a little too much time talking to coworkers, discuss some conversational exit strategies like, “sorry, I’d love to talk more but I have to get something done.” If they are overwhelmed with their workload, suggest ways to ask for help.

For task-based coaching, you may need to enlist help from a coworker. Employees need to know what a job well done actually looks like, which sometimes means letting them shadow their boss and see how to do it right. If singling people out feels like a bad idea, offer to let anyone on the team have a shadow session.

Accountability isn’t a one-time thing


Another thing Sir Whitmore’s model doesn’t address is how to avoid making accountability feel like an interrogation. This is where it pays to be both a boss and a friend.

If things aren’t improving after all the planning and goal setting, revisiting the problem has to be done with tact. It is mandatory to protect their feelings? No, it’s incumbent on every employee to listen to their boss and meet workplace expectations, but rapport can be a pleasant social lubricant.

Keep in touch with employees, that way if there has to be an awkward conversation, the criticism will go down easier because it’s coming from a friend. Since building friendships requires time and regular connection, make regular progress updates more fun by weaving in some funny memes or YouTube videos.

Ask a question like, “How have you been doing about ____ since we talked about it?” If things have reached the disciplinary action stage, be calm and direct about it, and let them know you’re here to help.

Probably the best advice for effective coaching is to make feedback a regular part of worker-manager relationships. That way when things get choppy, employees know their boss is there to support them, not demean them.

What Sir Whitmore didn’t address

Let’s talk about the real organizing principles of good coaching—being able to talk to people.

Nothing against Sir Whitmore’s GROW model, but discussing goals isn’t always the most effective way to increase team performance. Communication skills and emotional intelligence are what tip the scale from “I hate my boss scales” to “my boss wants to help me.”

Here are some things to consider when working through a coaching session.

Talk is not cheap

Managers walk the fine line of leading by example while tending to the well-being of their teams. Even though they are immersed in work, they have to also remain a relatable human.

Coaching works in much the same way. It is the art of candidly laying out the facts of the matter—including naming the mistakes made by the other person—while keeping things relatable, respectful, and encouraging.

Conversations like this can be difficult, especially if the mistake in question seems like a no-brainer that shouldn’t have happened (which happens a lot). Nobody likes feeling attacked or belittled, which is why criticisms must be delivered carefully if they are going to stick at all. When people feel anxious or afraid, they focus more on how to protect themselves than on whatever their manager is saying at the time.

Good coaching has to start with managers who can call out mistakes clearly while keeping the other person’s best interests at heart.

Asking good questions

If you’ve ever been called in for an unscheduled one-on-one, you know what it feels like to watch what you say. Guarded speech—on either end of the conversation—tends to prevent meaningful dialogue and often leads to open-ended questions that invite confession more than they help employee engagement.

Asking good questions is an essential coaching skill. No matter your coaching style, asking if someone likes their job won’t help you figure out why they keep saving files in the wrong company folder. Questions need a clear premise and lead to a specific discussion.

It also takes courage to ask good questions. But since we all deserve to receive direct feedback, it’s worth learning.

If you’re unsure about how to ask more direct questions, here are some suggestions on how to make vague questions more specific:

Rather than asking…

Is everything going alright?

Did you notice anything about that email you sent?

What are some ways you think you could improve?


What are some of your biggest challenges with work emails?

Are you aware that you misspelled “hitch” in your email to HR?

Do you think you might benefit from some weekly proofreading practice?

The right questions can become powerful ones if focused in a specific direction. Opening a conscious, focused dialogue lets coaches share their experiences without having to beat around the bush looking for an opening.

If you don’t know, ask

Questions are the secret sauce to keeping conversations fluid, and if you ask the right ones, they can yield helpful information without any of the awkwardness of a direct inquiry. Feeling stuck about how to frame a question? Here are some suggestions to keep things moving:

  • What do you say is the hardest part of your job?

  • If you had a magic machine to help you at work, what would it do?

  • What do you wish people understood about your job?

  • What does a perfect day at work look like?

  • Is there something you’d like more training on?

Put yourself in their shoes

There’s nothing like a good story. Sharing anecdotes can open doors and forge friendships you never expected because they are so undeniably genuine. Sure, maybe you knocked a project out of the park this year, but have you ever been embarrassed by your work? Those are the tales people relate to.

Again, managers walk a fine line of leading by example while relating to their teams. Team members in need of coaching often feel unsure about how well they are contributing, which is why it’s important for managers and veteran team members to periodically share the personal insights they gained through trial and error. Knowing that you made mistakes while in a similar position, but still managed to be successful can go a long way

Always find opportunities to sympathize and commiserate. Not only can they provide chances to share some hard-fought wisdom, but they can also forge bonds that strengthen teams.

When in doubt, break it down

One problem-solving staple is to break big plans down into manageable steps (though Sir Whitmore never mentions it). Anyone can dream big, but reaching those goals requires constant work and effort that can easily become overwhelming if not plotted out.

Gantt charts are a popular tool for big projects, as they lay out what should happen when, and they provide enough time for all of life’s little hiccups. The Agile methodology is another approach used by project managers to break major tasks down into clear, understandable steps.

The journey of 1,000 miles begins with a single step. Anyone can do hard things as long as they know how to make progress. Baby steps.

Why coaching matters

Nobody’s perfect, which means no one’s perfectly coachable, which means there’s no such thing as a perfect coach. If you want to get all psychological about it, transference is the place where psychologists say coaching really happens—where vulnerability and openness lead to true understanding and growth by sharing a little bit of soul with each other.

Coaching requires not just one, but both parties to see things from the other’s point of view. Take confidence in knowing you are out there to help people. Learn what they need and why they need you, and you’ll get results.