Filling in the Blanks: Managing, Coaching, or Mentoring?

Originally published June 2023. Updated July 2026.

You’re working on a crossword puzzle, and the clue for 13 Down prompts you with, “A leadership skill.” It’s an eight-letter word. C-O-A-C-H-I-N-G, you think. Hmm.

Or it could be M-A-N-A-G-I-N-G, right? You scan the other clues to guide your guess. 

You realize the first letter must be M, courtesy of 12 Across. M-A-N-A—oops, you counted wrong. There are nine open spaces, not eight. 

M-E-N-T-O-R-I-N-G, you write instead.

We often treat the terms managing, coaching, and mentoring as if they were interchangeable synonyms. They’re not, except possibly as answers in a crossword puzzle.

If you’ve ever overseen something—an account, a committee, or simply a collaborative task—you’ve written emails or given verbal feedback that turned the dial, consciously or subconsciously, to one of these three modes.

Each one signifies a different concept and, with that in mind, should guide you toward a different communication style. Here’s the breakdown:

• Managing emphasizes the execution of the project at hand.
• Coaching emphasizes a known practice that needs reinforcing. 
• Mentoring emphasizes underlying rationales for the practice.

Note that there’s no hierarchy of value. Effective leaders need all three modes. “Mentoring” isn’t universally better than “coaching,” nor is it automatically loftier than “managing.”

Sure, managing is the most utilitarian and can seem dismissive of other people’s authority. But coaching, if it’s not done correctly, can create needless rounds of coordinating emails that waste people’s time. And mentoring, under the wrong circumstances, can seem patronizing.

Pay attention to the cues of the specific time and place. These will dictate the specific mode you should use as a leader.

Managing should be the priority on a high-stakes deal with a tight deadline, with a major client, or both.

Coaching could be key when someone has been transferred to a new department or is on a rotation dedicated to building expertise.

Mentoring will be particularly meaningful for newer hires seeking to climb within their career or for interns who are destined to move on at the end of their term.

Let’s think about these concepts in action. Rather than framing this as a quiz with a single “right” answer for each scenario, judge for yourself what your instincts would be—and consider your openness to an alternate option of response. 

“Three Times” Is the Charm

A longtime client has come to you with a new invention, one for which they’ve already obtained a utility patent. It’s a handheld device that fights off sharks while the user (typically a surfer or snorkeler) is in the water. Your client is looking for guidance on the pitch to potential investors, including an appearance on a popular TV show one month from now, where they’ll be pitching—publicly—to wealthy investors.

Your co-worker, on a shared reply thread, says, “Fantastic! Let us know when you’re free for a meeting.” This response ignores your company’s best practices for scheduling meetings. What do you do?

• The “managing” response is to jump in—after checking the relevant in-house calendars—and suggest three specific dates and times. There’s not much time before their company falls under the hungry gaze of investors. 
• The “coaching” response is to wait a day and, when your co-worker receives no response to their email, suggest they follow up with three specific dates and times that work for everyone on your team who may need to attend. 
• The “mentoring” response is to tell your co-worker to use the rule of three when querying for meetings, to avoid choice overload. Based on their reply, you might expand (“I suggest different times of day”) or send a link to an explanatory article. 

Keep It Simple(r), Stupid*

*Note that Maestro Group doesn’t endorse addressing anyone using the nickname, “Stupid.”

After several unsuccessful cold calls to a big firm, your company has found an interested party on the inside who needs a software solution—and has purchasing power. Your co-worker sends an email that extols the features of your product, asks for a meeting, and attaches two case studies.

They don’t mention that, based on your initial analysis, this firm’s purchase of your software could save them $90K this year, and an average of $60–$70K each year thereafter, by eliminating redundancy in process and wasted market research. What do you do?

• The “managing” response is to call the contact as a follow-up to the email and mention the data on potential savings this year and thereafter. 
• The “coaching” response is to remind your colleague that initial analysis yielded a compelling number regarding savings, and they should use it in the next contact.
• The “mentoring” response is to discuss the concept of BLUF (“Bottom Line Up Front”), and make sure they understand the importance of foregrounding value to prospects.

Couldn’t Get a—in Edgewise

Your team is tasked with a set of audits for a company weighing the possibility of a merger. Significant pain points lead participants to take long pauses before they’re ready to answer your questions. During the first two interviews, you notice that your co-worker is quick to ask questions and then jump in, either with qualifying statements or follow-up questions, before the participant has finished or even started speaking.

This mannerism makes participants feel rushed and obscures important information. What do you do?

• The “managing” response is to suggest you take the lead on the next interview—with the CFO—because you can’t risk getting incomplete answers. 
• The “coaching” response is that you note the consistent reluctance of participants to answer, then reinforce the importance of getting as much information as possible. 
• The “mentoring” response is to relate that most people struggle with waiting after asking questions and share a tip (such as counting to five before speaking further). 

Roget’s Thesaurus was assembled by Peter Mark Roget (1779–1869), a British physician who was also a lexicographer. In 1805, he began keeping an informal notebook of words organized by meaning. In 1852, he published Thesaurus of English Words and Phrases, Classified and Arranged so as to Facilitate the Expression of Ideas and Assist in Literary Composition.

(He also wrote Animal and Vegetable Physiology Considered with Reference to Natural Theology, in case you’re looking to understand the interior of a tortoise better—page 467.)

His thesaurus is a massive achievement—but it doesn’t capture the nuances of managing, versus coaching, versus mentoring, that are specific to interactions in the contemporary workplace.

Your clue for 116 Across is, “What can your company achieve when your leaders are thoughtful about their chosen communication style?” The answer needs to fit in five letters. 

Can we suggest S-A-L-E-S?

What’s a 7-letter word for “expertise, command, proficiency, or prowess”? Contact mastery@maestrogroup.co so we can help you fill in the blanks.