How I Found Better Maintenance Supervisors after many failed attempts

Over the last 3 years assisting with operations across 1,600 apartments in 5 states, I have helped to recruit, hire, train, and develop numerous maintenance supervisors of varying talent levels. In doing so, I thought I would synthesize some of the lessons I learned along the way to help other operators with their recruiting process based on what I found worked well.

Vetting Past Results

References matter more than the resume. IF AT ALL POSSIBLE a word of mouth referral to “head hunt” a great supervisor who is locked up at another company is invaluable. You may get lucky sometimes, but many times the best talent is not actively putting out resumes during your hiring spree so without these word of mouth referrals you may not have access to them. If you have property managers or regular technicians that you trust and are performing very well, then ask them who their supervisor was at their last job and ask them for the contact info so you can reach out to plant a seed/start a conversation. Ask your GC who they interface with that is awesome at other companies and try to find out that way. Ask your HVAC supplier who comes in often and is organized and in charge at another company doing apartment work.

Read the resume for objective measures that match your operation. Converting 10,000 sq ft of warehouse space into office use is a real accomplishment. It tells you nothing about whether someone can execute 50 apartment turns per month on a repeatable schedule. Match their past scope to your actual scope as closely as you can. This is the “been there, done that” factor. If they come in with the knowledge you need (and sometimes even more) they will show you what it is like to hire “A” talent. I have had this in my last 2 supervisor hires and they both stabilized their assets in a way that no supervisor before them could. One stabilized a highly distressed 250 unit portfolio with a few subordinates and coordinated all the subcontractors for 100+ unit turns in his first 9 months, while the other has taken on and stabilized 900 units with minimal hand holding and improving the talent level of all technicians he oversees through accountability and clear communication.

If the resume claims a specific capability (supervised 22 direct reports, managed a $2M maintenance budget) ask about it directly. With AI helping to create job descriptions for HR and recruiters, it is also helping technicians make their resumes. Ask them to verbalize what they did and how they did it so that you can see if they actually understood it. A lot of things like this get listed and you find out that they had a supervisor/manager above them doing most of the leg work and that this supervisor was acting more as a senior technician turning a wrench most of the time. Not a bad thing, but if you need someone to oversee things at scale they have to understand how to do that implicitly and not be asking you how to do their job every day for the first 6 months.

HR and People Management Questions to Ask

How do you track time and manage overtime?
How do you handle chronic tardiness or employees who exhaust PTO and keep calling out?
Who owns PIPs, write-ups, and terminations on your team, you or HR?
How involved are you in recruiting and onboarding?
How do you measure productivity across your team? What KPIs do you use? What software do you pull those from?
On a scale of 1–10, rate your working knowledge in HVAC, plumbing, and electrical.
In your last role, were you primarily in the field or behind a desk managing outcomes? Which do you consider your stronger mode of operating?

Defining the Role Before You Post It

The supervisor role varies widely across operators:

1–2 techs, 80–200 units: primarily hands-on, working supervisor
3–10 techs, 200–800 units: split between field and oversight
10+ techs, 1,000+ units: primarily managing people and systems

Your job description has to be honest about which of these you're hiring for. If the role is hands-on and the candidate spent the last three years as a project manager who hasn't touched tools since, verify they're willing to go back to working alongside the crew. Plenty of candidates have the knowledge but won't take a step back in that direction. They'll leave within six months when the reality sets in.

The inverse is also a real hiring risk. A tech with 20 years in the field who wants to move into supervision needs to demonstrate three things before you make that bet:

Technology fluency: Can they use your platforms (property management software, project management software, HR software, etc) now, or have they at least used something similar in recent years, and used it to a similar degree and frequency as you will need them to use it?
A learning track record: Have they pursued certifications on their own? Taught themselves anything outside of what a job required? Demonstrated curiosity tends to show they want to learn more and set themselves apart. Your best supervisors are great leaders and team players, and they also have a drive to prove something and outperform every other tech.
Evidence of leading people: Have they trained someone, corrected someone's work, run a crew, spot checked, followed up on projects? Using technical knowledge to produce outcomes through other people is a different skill than producing outcomes yourself. Look for any concrete example of this, ideally mirroring what you need them to do with your team.

Deciding What the Role Is Responsible For

Before the interview, answer this question for yourself: Is this supervisor primarily responsible for data (pulling reports, holding techs accountable to entering time and materials, analyzing turn times, building KPIs, presenting to leadership)? Or is their primary job on-site execution?

You can't get both at full capacity from one person without paying for it. A supervisor spending 80%+ of their time in the field turning wrenches, scoping work, and directly managing techs is not going to spend evenings building dashboards and refining KPI frameworks. If you need both, you're either hiring two roles, stacking the compensation to attract someone who can genuinely do both, or accepting a trade-off in one direction.

Technicians who have developed real data and systems skills (KPI ownership, report building, process design) earned those skills through deliberate effort. They will price themselves accordingly. If you want that profile, budget for it. If your operation doesn't need it yet, don't hire for it and then underpay and wonder why the candidate leaves.

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