Growing Frontline Managers in Operations: COOs Share What Signals Readiness

14 ownersVaibhav Kakkar, Jason Hennessey, Sean Smith, Arvind Rongala and 10 more

Anticipate Second-Order Effects

Vaibhav KakkarFounder and Group CEO, Digital Web Solutions

The milestone we trust most is when someone starts thinking about second-order effects. Strong contributors can solve the problem in front of them with confidence every day. Future managers think about how each decision affects workload, morale, speed, and customer experience. That wider view matters more than charisma because good operations depend on steady foresight.

We test this by involving them in recurring challenges without perfect answers every time. We watch how they balance competing priorities and explain each tradeoff with clarity, calmly. We also look at whether they keep the team aligned after the decision, together. When they handle ambiguity without spreading stress, they begin protecting the system that supports everyone.

Build Changes That Endure

Jason HennesseyCEO, Hennessey Digital

The wrong way to identify new frontline managers is to ask who works hardest. The right way is to ask who leaves the operation clearer after touching it. Emerging leaders create fewer exceptions, document what good looks like, and surface risks early enough that fixes stay inexpensive. That is how capacity grows without putting daily performance at risk.

I trust one milestone more than any title recommendation: when a person can run a cross-shift improvement that sticks after attention moves elsewhere. Plenty of people can launch a change. Far fewer can embed it so adoption survives fatigue, turnover, and competing priorities. Sustainability, not enthusiasm, is the trait that predicts success in larger operational scope.

Prove Readiness Through Trainee Success

Sean SmithFounder & CEO, Alpas Wellness

By providing developing managers with the responsibility of mentoring incoming new hires into all non-clinical roles in the organization, we create a "real world" opportunity for them to test their ability to develop coaching behaviors. As such, they can demonstrate these behaviors without having to sacrifice their current operational responsibilities. The measurable milestone of an emerging leader's readiness for increased scope will be demonstrated by the fact that their assigned trainee has reached full administrative productivity before the scheduled time frame with no compliance errors. Demonstrating success through someone else represents a fundamental shift in thinking from being an individual contributor toward a focus on team performance and quality assurance.

Delegate Without Becoming a Bottleneck

Arvind RongalaCEO, Edstellar

The strongest signal that an emerging frontline manager is ready for broader responsibility is not consistently delivering strong individual results—it is creating strong results through others without becoming the bottleneck. A practical milestone is sustained delegation: an employee can step away from day-to-day decisions while the team maintains service levels, resolves routine issues, and stays on target. Preparation should combine stretch assignments, coaching practice, and ownership of a small operational improvement, with performance measured through team outcomes rather than personal output. McKinsey research found that frontline managers often spend only 10–40% of their time actually managing and coaching employees, while organizations that emphasize coaching report stronger frontline-manager performance. In operations, readiness becomes visible when a manager starts anticipating problems, developing people to solve them, and improving the system rather than simply being the person who fixes every problem.

Own Problems Unprompted

Joe SpisakCEO, Fulfill.com

I promoted someone to warehouse manager at 24 who everyone thought was too young. He'd been with us eight months. Best decision I made that year, and here's why: he'd already started solving problems I didn't know we had.

The signal wasn't tenure or technical skill. It was ownership without permission. This guy noticed our receiving team was getting slammed every Tuesday because certain brands shipped their weekly inventory on the same day. He mapped it out, called three of our clients directly, and convinced two to shift their delivery window. Our Tuesday bottleneck disappeared. I found out about it two weeks later when I asked why receiving looked so smooth.

That's the milestone I look for: when someone starts managing up instead of waiting for direction. They bring solutions, not problems. They've already built relationships across departments. Most importantly, they're making your job easier without you asking them to.

Here's my actual promotion test at the fulfillment company. I'd give a high-potential person a contained project with real consequences. Not busy work. Something like: we're adding a new client with specific temperature requirements, figure out what equipment we need and build the onboarding process. Then I'd watch how they handled ambiguity. Did they ask me to solve every decision or did they research, propose options, and own the outcome? The ones who came back with a full plan and said "here's what I recommend and why" got promoted. The ones who kept asking "what should I do next" needed more time.

The mistake most founders make is promoting based on performance in the current role. Your best picker might be a terrible pick supervisor. I learned to separate execution skills from leadership capacity. Can they teach someone else to do their job? Have they already started doing it informally? When they're on vacation, does their area fall apart or keep running?

One practice that saved us: I made every manager-track person run our weekly all-hands meeting at least once. You learn instantly who can command a room, synthesize information, and make fifty people care about the same goal. It's a low-risk audition for the real thing.

The best operators don't wait for a title to start leading.

Test Management Behaviors Early

Ben CollierCo-founder, Ocasta

I wouldn't promote someone into management just because they're the strongest performer. Performance tells you how well someone does their current job; behaviour gives you a much better indication of whether they're ready for the next one.

We'd look at what good management actually looks like in that operation, then observe for those behaviours in real work. Can they coach someone well, make a sound judgment under pressure, and keep standards up without constant direction?

The strongest signal is consistency. Don't wait until someone becomes a manager to find out whether they can manage. Give them parts of the role early, observe how they handle them, and use any gaps to target the coaching or learning they need before the promotion happens.

Audit Crew Output to Prove Judgment

Carolyn VasquezFounder, Ready Rental Cleaning

The milestone I watch for is a cleaner catching a mistake on someone else's job before I do. Every clean gets photographed room by room, so the checklist leaves a record I can check later, not just a memory of how it went. When someone starts flagging a missed photo or a skipped step on another crew's turnover, without being asked, that tells me they understand the standard beyond their own job. Tenure alone has never told me that. Before I hand someone a second crew, I have them audit a second crew's photos for a week first. They compare what got missed against what should have passed, and they never touch a spray bottle on that job. If their calls match mine on what needs a redo, the extra capacity comes with the same eyes checking twice the work. If their calls miss something, I find out before a turnover goes wrong instead of after a host complains. A frontline promotion based on speed or seniority usually costs a home its next booking. One based on judgment I can watch and score usually doesn't.

Grant Authority to Reveal Decision Quality

Dane MaxwellFounder, Paperless Pipeline

We have no management layer, so the next step for someone here means owning an area rather than getting people to report to them. The readiness question is the same either way. Can this person make decisions in the open, without checking first, and be right often enough that the wrong ones stay cheap.

The practice that surfaces it is handing over real authority early, bounded, and then watching. Our first support hire was told she could refund a customer up to $500 on her own reading of the situation, without asking me. I did not review those afterwards, which is the whole point, because a decision you have to justify to me is not a decision, it is a recommendation with extra steps.

The milestone I look for is not a good week. It is a bad one. The signal is somebody getting through the worst week of the season, when everything lands at once, escalating almost nothing, and the few things they do bring me being the right things. Anyone looks ready when the queue is short.

The reverse signal gets missed. A person who never escalates anything is not ready either; they are hiding. I have handed an area over on that basis once and spent the following six months discovering what had been quietly going wrong in it.

Give the authority first. Readiness is what people do with room, and you cannot see it in anyone who has never had any.

Entrust Costly Decisions Within Safe Bounds

Neill David WatsonFounder, APMZEE

I prepare people by handing over a decision that costs money, not by sending them on a course.
The mistake I made early was promoting on the strength of somebody's own output and hoping the management part would arrive later. It does not, and you find that out during a bad week. So now the preparation happens before the title, in the open, with something real attached. At APMZEE that meant giving one person the reorder decision for a product line, including the budget and the consequences of getting it wrong, while I stayed available and deliberately quiet.
Day to day performance is protected by keeping the scope narrow and time limited. One line, one quarter, one thing that can go wrong in a way the business can absorb. That is a different proposition entirely from handing somebody a team and finding out afterwards.
The milestone I trust is the first time they tell me no, with a reason, and hold it. Before that point people are carrying out your judgement with their hands. After it they are using their own, which is the whole job.
It happened with that reorder. I pushed for a bigger buy on a line I liked personally, she declined and showed me the sell through week by week, and she was right by a distance. The order I wanted would have left us with roughly 30% more stock than we sold that quarter. She has run her own area ever since.

Validate Capacity With Clean Handovers

Kanchan GuptaC-Founder and COO, CADRE ODR

The people worth backing usually start behaving like managers before anyone gives them the title. They'll flag a problem before it reaches me, or quietly fix the handover that keeps breaking. Capacity gets risky when you hand over a title and walk away, so I prefer to give scope in pieces.

The milestone I trust is a clean handover. Let someone own one full process end to end, reporting included, while they still carry their existing work for a set period. If the numbers hold and they've trained a backup, they're ready. If the numbers only hold because they're working fourteen-hour days, that's stamina, not readiness.

The harder part is watching your own judgement. There's a bias I've seen often: a man scoring six out of ten against a job description reads as promising, while a woman at the same six reads as not a fit. The gap sits in our heads, not in the evidence. Decide what proof you need first, then hold everyone to it.

Transfer Real Ownership in Stages

Siim KostabiFounder, 3Dstudio.co

One signal I've learned to trust: they start solving problems before telling me about them. Not hiding things, just not waiting for permission to think.

At 3D Studio, when a senior artist started fielding client revision requests directly and looping me in after the fact with a clean summary, that was the moment. They weren't asking "is this okay?" They were reporting what they did and why. That shift in posture told me more than any performance review.

The preparation side is less glamorous. I give the person one thing that's mine: a client relationship, a deadline call, a vendor negotiation. Not a test, just a real transfer. If they handle it without drama, I extend the scope. If something breaks, we debrief on what they'd do differently. The debrief matters more than the outcome because it shows whether they're building a mental model or just executing tasks.

The mistake I made early was promoting people who were excellent at their current job and then being surprised when the new scope exposed a gap. Technical skill and operational ownership are different muscles. The ones who were ready had already been doing small versions of management informally, before any title changed.

One milestone that consistently meant something: when other team members started going to them first.

Credit Teammates and Lead Shared Rituals

Vincent NeroVP General Manager, Successories

The signal we trust most: the person starts crediting other people without being asked.

Strong individual contributors talk about what they finished. The ones ready to lead start saying "that was mostly Dana's catch" in a status update where nobody prompted them. It is a small thing, and it is hard to fake, because it means they are watching the work of people around them instead of only their own queue.

The practice we use to prepare them is deliberately low-risk. Hand them one recurring responsibility that belongs to the team rather than to a project, such as running the weekly handoff or owning the recognition for the team's wins that month. They get real ownership, the daily output does not depend on them getting it right immediately, and you find out fast whether they can hold a group's attention. If that goes well after a quarter, widen the scope. If it does not, nothing broke.

Document Procedures Others Can Execute

KEITH YUNXI ZHUChief Executive, TKEG Expat INC

TKEG Expat is a corporate-services firm that manages 120 companies across 22 jurisdictions, and most of our operations work is regulated filing work where an error is expensive. Therefore, instead of identifying emerging frontline managers by who performs the best, we identify them by who can hand their own work to another person without the quality moving.

For our company, TKEG Expat, the day-to-day risk is contained by a maker and checker rule that we wrote down. Whoever drafts must discover every figure field-by-field from the actual downloaded authority form, pin every answer to a specific tax period, and cite an authoritative source for every rate, rule or deadline, and the work can not leave draft until I sign it off. Which means the preparation is the drafting itself, we widen someone's scope early because the scope they gain is drafting scope, and the sign-off does not move.

The milestone that signals readiness is the write-up instead of the filing. After a filing is actually completed, the person who performed it writes the reusable procedure for it, and our standing instruction is to read the relevant procedure before starting and add to it after finishing. We keep 8 live standalone filing-procedure documents across four country trees, each carrying a dated line naming the real filing it was distilled from. Most of the times, when an operator produces a procedure the next person can file from without asking me anything, I'd say that operator is "ready" for the next scope.

Resolve Friction Across Departments

Scarlett KennedyExecutive Director, Maplewood Treatment Solutions

We are developing frontline admin leadership through delegation to candidates in charge of certain aspects of implementing new workflows and rolling out various software system updates. As we delegate responsibility for these types of small-scale tech deployments (and as they build their project management capabilities), we can keep the operational systems stable at the same time. The milestone which represents that a candidate has shown a level of readiness for "next-level" leadership is when a candidate demonstrates the ability to resolve departmental scheduling and/or communications friction on their own directly with peer leads without needing executive involvement. In addition to demonstrating mastery over peer diplomacy (the art of facilitating collaboration/communication among peers) and cross-functional alignment, an emerging manager demonstrates that they can provide stability within operations as they expand into larger areas of responsibility.

Q&A

Growing Frontline Managers in Operations: COOs Share What Signals Readiness

Q&A

Growing Frontline Managers in Operations: COOs Share What Signals Readiness

Anticipate Second-Order Effects

Build Changes That Endure

Prove Readiness Through Trainee Success

Delegate Without Becoming a Bottleneck

Own Problems Unprompted

Test Management Behaviors Early

Audit Crew Output to Prove Judgment

Grant Authority to Reveal Decision Quality

Entrust Costly Decisions Within Safe Bounds

Validate Capacity With Clean Handovers

Transfer Real Ownership in Stages

Credit Teammates and Lead Shared Rituals

Document Procedures Others Can Execute

Resolve Friction Across Departments

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