Let me guess how your first real mentoring session went. You showed up ready to grow, your mentor asked what you wanted to work on, and you froze — because the honest answer was "everything." Communication, confidence, that thing you're bad at in meetings, the technical stuff, the leadership stuff, the whole pile. When the list is that long, most people do the worst possible thing: they try to nibble at all of it at once and end up moving none of it. The problem was never a shortage of things to fix. It's that nobody taught you how to pick.
Article Summary
I've been on both ends of this. I started my first job at 17 and spent decades on the factory floor and up through leadership at some big companies, and for a long stretch I was the guy who wanted to get better at all of it at once. Give me a book on every weakness. Sign me up for every workshop. It felt like progress. It wasn't. I was busy, not better. It took me an embarrassingly long time to learn that growth isn't about how many skills you're chipping at — it's about aiming your limited time at the one that actually unlocks the rest. That's what this whole article is about: how to aim.
Why "Work On Everything" Is a Trap
Here's the math nobody wants to hear. You have a finite amount of time and attention. Your mentor has even less to give you. If you split that thin slice across eight skills, each one gets a sliver too small to make a dent. You'll feel motion — you're doing stuff, you're taking notes, you're "working on yourself" — but three months later nothing has really changed. Spreading effort feels responsible. It's actually the fastest way to stall.
There's a second trap hiding inside the first one: the skills that shout loudest usually aren't the ones that matter most. The thing that's embarrassing you this week, the skill your buddy just bragged about, the shiny new tool everybody's talking about — those grab your attention, but grabbing attention isn't the same as unlocking growth. If you let the loudest problem set your agenda, you'll spend a year fixing symptoms and never touch the root. A good growth plan is quiet and boring and pointed. It ignores the noise on purpose.
So before you ask your mentor to help you get better at anything, you've got to do the unglamorous work of choosing. Not choosing everything. Choosing the few. And choosing well starts with a handful of honest questions.
Three Questions That Narrow It Fast
When a list feels overwhelming, you don't need more options — you need a filter. These three questions are the filter I come back to, both for myself and for the leaders I coach. Run your long list through them and watch how fast it shrinks.
Question one: What's actually holding me back right now? Not what would be nice to have someday — what's the specific thing standing between you and the next step you're trying to take. If you want that promotion and every time you open your mouth in a room full of executives you shrink, then it doesn't matter how good your spreadsheets are. The thing in the doorway is the thing to work on. Name the doorway.
Question two: Which skill, if I got noticeably better at it, would make three other things easier? Some skills are lonely — they help with exactly one situation. Others are multipliers. Get better at asking clear questions and suddenly your meetings, your relationships, and your problem-solving all improve at once. Look for the multiplier. That's where your scarce time earns the most.
Question three: Where does my mentor actually have something rare to give? Your mentor has specific scar tissue. If they built the exact kind of team you're trying to build, or survived the exact transition you're staring down, that's gold you can't get from a book or a video. Point your mentoring time at the places where their lived experience is the whole point. Don't burn a rare resource on something you could have Googled.
The Three-Question Filter
- What's in the doorway? The skill that's blocking your very next step beats the skill that would be "nice someday."
- What's the multiplier? Pick the skill that makes three other things easier, not the one that helps in a single narrow spot.
- Where is my mentor rare? Aim at the stuff only their real experience can teach — don't waste it on what a search bar could answer.
- The overlap wins. When a skill checks all three boxes at once, stop looking. You found your focus.
Find the Keystone Skill
In an old stone archway, there's one wedge-shaped stone at the very top called the keystone. Pull it out and the whole arch collapses. Set it right and every other stone holds. Skills work the same way. Somewhere in your long list is a keystone — one skill that's quietly holding up a bunch of the others. Find that one, and a lot of your "separate" problems turn out to be the same problem in different clothes.
Let me make it concrete. A younger version of me thought I had a dozen unrelated weaknesses: I avoided hard conversations, I over-explained, I struggled to delegate, I took feedback like a punch. Twelve problems, right? No. They were one problem — I hadn't learned to be direct and calm at the same time. That was the keystone. Once I worked on that single thing with people who could model it for me, half the other "weaknesses" loosened up on their own, because they'd all been leaning on the same missing stone.
Finding your keystone is worth slowing down for. Look at your list and ask: which of these, if I fixed it, would make the others matter less? Which weakness shows up over and over in different situations? That repetition is a clue. The skill that keeps showing up in disguise is usually the one worth pouring your mentoring hours into. Nail the keystone and you're not fixing one thing — you're pulling the whole arch into place.
Keystone or Just Loud?
A quick gut check: a loud skill embarrasses you in the moment — you fumbled a presentation, so "public speaking" jumps to the top of the list. A keystone skill shows up everywhere — the real issue might be that you don't prepare your thinking before you speak, which also wrecks your emails, your one-on-ones, and your decisions. Loud fixes one bad afternoon. Keystone fixes a pattern. When you're not sure which you've found, ask: "Does this weakness only bite me here, or does it keep showing up wearing different outfits?" The one wearing different outfits is your keystone.
Use Your Mentor to Pick, Not Just to Teach
Here's a move most people miss: your mentor can help you choose the target, not just hit it. You don't have to walk in with the perfect skill already picked. Some of the best mentoring conversations I've ever had started with me saying, "Here's my whole messy list — help me see what actually matters." A mentor who's further down the road can often spot your keystone faster than you can, because they've watched people with your exact blind spot before.
Try bringing them the raw list instead of a polished plan. Say the embarrassing stuff out loud. Then ask the question that unlocks their perspective: "If you were in my shoes, which one of these would you work on first, and why?" That "and why" matters — the reasoning teaches you how to prioritize for the rest of your life, not just today. You're not only getting an answer. You're borrowing their judgment about what's worth chasing, which is a skill all its own.
One caution, learned the hard way: don't let a good mentor turn into an excuse to keep collecting instead of committing. It's easy to have a great "what should I focus on" talk, feel productive, and then have the same great talk next month about a different shiny skill. At some point the picking has to stop and the working has to start. A mentor helps you aim. But you're the one who has to pull the trigger and actually put in the reps — which is exactly where the underlying Law comes in.
Why This Is Really the Law of Design
One of John C. Maxwell's 15 Laws of Growth is the Law of Design, and it says this: to maximize your growth, you have to develop strategies. Growth left to chance stays small. You don't drift into becoming better at the right things — you have to plan it. And that's the real answer to "what skills should I focus on." The question isn't really about skills at all. It's about whether you have a strategy or you're just reacting to whatever's loudest that week.
Think about what you're actually doing when you pick a keystone skill and aim your mentor at it. You're designing your growth on purpose instead of letting it happen by accident. You're saying, "Of all the things I could do, here's the one I've decided is worth my best hours, and here's why." That's a strategy. It's the difference between a person who spends five years busy and a person who spends five years better. Same effort, wildly different results — and the only variable is whether there was a plan behind the effort.
I've lived both versions. Across a career that ran from the factory floor up through Coca-Cola, Estée Lauder, AmerisourceBergen, and now Oerlikon, where I'm an Engineering and Reliability Manager, my worst growth years were the ones where I worked on whatever was in front of me with no plan behind it. My best years were the ones where I got deliberate — picked the one skill that mattered most for the season I was in, found people who could teach it, and stayed on it until it stuck. That deliberate design is a big part of what I ended up writing about in Leadership Between the Lines and teaching in the LBL-10 workshop. A mentor is a gift. But a mentor without a strategy is just a nice conversation. Give them a target, and now you've got a plan.
The Quick Version
Don't try to work on everything — that's the trap that keeps you busy and stuck. Run your list through three questions: What's blocking my next step? Which skill multiplies the others? Where is my mentor's experience truly rare? Look for the keystone — the weakness that keeps showing up in different disguises — and aim your mentoring hours there. Let your mentor help you pick, not just teach, and then commit and put in the reps. That's the Law of Design: to maximize growth, you build a strategy instead of reacting to whatever's loudest.
Reflection Questions
Sit with one or two of these before your next mentoring session:
- If I had to pick just one skill to work on for the next 90 days, what would it be — and why did that one come to mind first?
- Which of my weaknesses keeps showing up in different situations? Could that be my keystone?
- Am I choosing skills because they matter, or because they're the loudest embarrassment this week?
- Where does my mentor have rare, hard-won experience I've never actually tapped?
- Do I have an honest growth strategy right now, or am I just reacting to whatever lands on my desk?
The Bottom Line
So how do you know what skills to focus on with your mentor? You stop trying to fix everything and start hunting for the few things that move the most. You find the doorway you're stuck in, the skill that multiplies the others, and the place where your mentor's experience is genuinely rare — and where those three overlap, you've found your focus. Better yet, look for the keystone: the one weakness quietly holding up all the rest, the one that keeps showing up wearing different outfits. Fix that, and problems you thought were separate start solving themselves.
Here's what I'd do this week: write down every skill you think you should work on, the whole messy pile, and bring it to your mentor. Don't ask them to teach yet. Ask them to help you choose. Say, "If you were me, which one of these would you work on first, and why?" Then pick one — just one — and commit to it long enough for it to actually change something. That's not settling for less. That's designing your growth on purpose. And a plan you actually run beats a hundred good intentions you spread too thin every single time.
This ties back to The Law of Design — one of John C. Maxwell's 15 Laws of Growth.
About Jay Olivo
Jay is a John Maxwell Executive Coach, DISC consultant, and CPMM-certified reliability leader with a career spanning Coca-Cola, Estée Lauder, AmerisourceBergen, and Oerlikon. He's the author of Leadership Between the Lines and creator of the LBL-10 workshop. Jay learned leadership on the factory floor, not in a classroom — and writes with Heart, Humor, and Help. Read Jay's full story →
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