The Toronto Maple Leafs are in the market for a new GM, and probably a president too. I’m offering my services.
No, not for the jobs themselves. But I’m willing to act as a consultant for the interview process. Specifically, I’ve got a few questions that I’d love to see Keith Pelley and his hiring committee ask potential candidates before making a decision on who’ll lead this franchise into the future.
Normally I’d charge a hefty fee to a corporate client for this sort of insight, but given the critical importance hanging over the coming decisions, I’ll make it a freebie. As my gift to the team that’s brought me so much joy over the years, here are the eight questions I wouldn’t let a candidate leave an interview without answering.
I’ll skip the obvious ones, such as “Rebuild or reload?” or “What should we do with Auston Matthews?” or “Who’s the coach?” Those are important, but even Pelley doesn’t need my help to come up with them. Let’s dig a little deeper.
“We just went from being 108-point division champs to missing the playoffs entirely. What do you think went wrong for us this year?”
Many of these questions won’t necessarily have right or wrong answers. This one absolutely does.
The wrong answer is the one MLSE has been trying to spin for the last few months: that this was a very good team that ran into some bad luck with injuries, made worse by a condensed schedule and a handful of off-years by otherwise reliable veterans. The implication is that the fix might be no fix at all, but rather a bit of patience combined with faith that this season was the outlier.
The truth, of course, is much less reassuring. It’s that last year’s team, while certainly better than this one, was one boosted by unexpectedly strong goaltending and an unsustainable record in one-goal games, and the regression in both categories was to be expected. So were injuries, especially with a roster this old.
In other words, you shouldn’t have been surprised when things started going south. And if it’s actually true that you were, then that says there’s something badly wrong with your process.
Consider this question a test. Will the candidate look you in the eye and tell you the truth, even if it’s not what you want to hear? Or will they blow smoke up your behind? If it’s the latter, that tells you what you need to know: You’ve got the wrong person.
“What would you expect your first month on the job to look like?”
Maybe this is a softball, because there are a ton of answers we’d be just fine with hearing. You’d expect something about firing Craig Berube and finding his replacement, maybe reorganizing the front office, planning for the draft and working on trades. Honestly, we’re fine with any of it.
Here’s the one thing we don’t want to hear: anything about how a month isn’t long enough to do much of anything.
That was the trap they fell into when they hired Brad Treliving in May 2023, with a full month to go before Mitch Marner’s NTC kicked in. The Leafs could have done something about that situation then, but didn’t, and fans were told there just wasn’t enough time. The new guy had to get settled in, and all that.
Nonsense. A month is forever in a short NHL offseason. Or at least it should be, to any executive who’s ready and willing to hit the ground running.
If the answer here sounds like a plan, that’s good. But if it contains anything like “I’ll need time to get the lay of the land first,” then you can thank the candidate for their time and inform them that they’re not a good fit. This organization has a huge hole to dig out of, and it can’t waste yet another summer working up the courage to get started.
Speaking of taking action …
“Tell me about a time you made a big, bold decision, and how it turned out.”
This one could be considered a bit of a trick question, because we’re not really interested in the second part. Instead, we want to know what the candidate’s definition of big and bold is.
Put simply, today’s MLSE seems like an organization incapable of taking big swings. Jonas nailed it in a recent piece, writing that “Treliving made no transformative swings in his three seasons as Leafs GM, no big, bold actions to lift the team to new heights.” That’s true, but it hardly seems like fair criticism, since you could argue Treliving was just slipping seamlessly into the corporate culture.
Time and time again, when faced with the chance for bold action, the Leafs punt. They take the path of least resistance. Whether it was firing Sheldon Keefe after multiple playoff failures, trading Marner in 2025 or moving on from Brendan Shanahan before his contract expired, the organization always kicks the can down the road until it’s too late for a decision to have any meaningful impact. Even the one move that could fall into the category of bold, parting ways with Kyle Dubas, was more about messy egos than what was best for the team.
And over and over and over again, all that hemming and hawing ended up costing the franchise. Today, the bill has more than come due.
By asking this question, we’re trying to achieve two things. First, to make sure any candidate understands what a big swing even looks like, and is able to make the case for the thought process that leads to one. And secondarily, but still importantly: to remind the other people in the room that yes, it really is possible to embrace action instead of fearing it. (You’d think their recent playoff history would have already done that, but here we are.)
No one, not even young star Matthew Knies, should be safe on this roster. (Troy Parla / Getty Images)
“Who on this roster would you consider untouchable?”
You can guess the answer we’re looking for here: Nobody.
Not after that mess of a season. Not after a decade of playoff disappointment. And certainly not in the middle of a Stanley Cup drought that’s about to hit 60 years.
Can you trade everyone? Of course not. And it’s perfectly reasonable to point out that guys with big contracts and trade protection are very, very hard to move in today’s NHL. This team has at least a few players for whom it’s difficult to imagine a realistic trade scenario coming into focus.
But untouchable? As in, you wouldn’t even listen to an offer if another team called? There’s nobody here who’s earned that. Nobody is even close. Not Matthews, not William Nylander, not Matthew Knies, not anyone. And any candidate who can’t get this question right shouldn’t need to waste everyone’s time with a long interview.
“Is Toronto a tougher market than others in the league, and if so, how would you deal with that?”
The narrative of Toronto being a brutally tough market to play in — and by extension, to win in — has been around forever. It shifts constantly, never quite able to decide if the fans are too demanding or not demanding enough, and it starts to fall apart when you look at other, even bigger markets around the sports world that seem to do just fine. But it’s certainly out there. So ask about it.
We’re doing two things with this question. First, we’re hoping we can find a candidate who calls B.S. on the whole thing. (Believe me, the first Leafs employee to do that, loudly and publicly, will be embraced as a hero by the fan base.) But more importantly, the second half of the question is making it clear that whoever we hire is going to be expected to deliver.
Is Toronto a tough market, one that’s really too big and scary to attract top talent? Fine, then what’s your plan for that? Because if you don’t have one, beyond shrugging and mumbling about how hard your job is, then you’re not a candidate. This market is what it is, and if it seems like too bright a stage for you, then don’t waste our time.
Ask the question. Get the answer. And then make sure the candidate knows you’re not especially interested in hearing any more about the topic.
But since we’re on the subject of the unique nature of this job, let’s come at it from the other side …
“We have an enormous financial advantage over almost every other team. How will you exploit that?”
The Leafs bring in more revenue than just about any other team in the history of the league, and while a hard cap puts limits on how much of that can be spent on players, pretty much everything else is fair game. (And with the cap soaring in the years to come, even roster-building advantages will start to open up.)
That doesn’t mean you can just throw money at every problem. In fact, a front office can be too crowded. You could argue that the current Leafs, featuring a staggering five assistant GMs and two senior advisers, have already crossed that threshold. But that doesn’t mean that money can’t be spent wisely. And that’s a huge advantage for the Leafs, who have more to spend than anyone else.
Or at least they should. If Pelley and friends are truly more focused on the bottom line than anything else, then this team is probably doomed and it won’t matter who they hire. If they really plan to nickel and dime this team over dollar amounts that add up to a rounding error for a corporate behemoth such as Rogers, then this is all pointless and they’ll get what they deserve — not just losses, but a Rogers brand that starts to look like poison to a huge swath of its customer base.
Asking this question would get some valuable insight from a candidate, while also strongly implying that they’ll have a blank check to work with as they build the organization back into a winner. Anyone who takes the job can make sure the bosses remember what they promised.
And speaking of the bosses, here’s one more question to ask …
“Are there too many people in the room right now?”
Pelley sounds like he’s going to be driving this process, and maybe he’ll handle the first round of interviews on his own. But this being MLSE, we can guess that eventually a candidate is going to have to meet with a room full of suits, each of whom secretly (or not-so-secretly) thinks they know more about the sport than a hockey lifer ever could.
So let’s hear what our candidates have to say about how this organization does business.
After all, that’s one explanation for the lack of bold decision-making we mentioned earlier. We can chalk it up to risk-aversion, but maybe it’s more like paralysis by analysis, the dreaded case of way too many cooks. The old corporate saw about how nothing good ever came from a committee has a lot of truth to it, but apparently, the suits at MLSE haven’t heard it. Or maybe they just think they’re too smart to fall into the trap.
Let’s ask the candidates about it. Put them on the spot, maybe even make them a little uncomfortable. And then see if they reach for the easy, mealy-mouthed answer about open-door policies and the importance of hearing from lots of different voices.
The correct answer, instead, will be something along the lines of: “This is a big hire, and I don’t mind you involving whoever you think is necessary to make this decision. But once I have the job, I don’t want to see or speak to 90 percent of you ever again. Unless and until it’s at a Stanley Cup party.”