Managing Expectations and the Meaning of Confidence

I don’t think that too many people would argue that Tom Ricketts isn’t a good businessman.

If his Wikipedia page is to be trusted, Ricketts was a success in the business world irrespective of his father’s prodigious efforts at TD Ameritrade. After taking his MBA at the University of Chicago, the younger Ricketts made his bones working at various financial firms, and pioneering the use of the Internet to help his clients sell their investment-grade bonds directly to retail customers. In 1999, he co-founded Incapital, a successful investment bank, for which he remains the Executive Chairman.

So you’ll forgive me if I chuckle to myself when people suggest Ricketts bit off more than he could chew financially by, together with his family, buying the Chicago Cubs. The guy plain knows how to make wise investments and run a business – I’m certain the same will be true of his investment in the Cubs.

But the question that we’ve still never been able to answer is whether he plans to run the Cubs a little too much like a business. Will he focus more on the bottom line than on-field success? Will he spend on payroll even if it isn’t a sound financial move? Will he manage his front office with the heart of a fan or the stolid approach of a Fortune 500 executive? (well, a Fortune 500 executive not named Mark Cuban, that is…)

We still don’t know fully how Ricketts’ business skills and background will inform his ownership of the Cubs, but I think we finally got a meaningful window during his pre-game, State of the Cubs press conference last night.

And, despite what you might think, I liked what I heard.

In addition to expressing confidence in manager Mike Quade, confidence in the team’s future performance, confidence in the team’s finances, confidence that attendance will come back, and confidence in the organization’s ability to field a good team in 2012 and beyond, Tom Ricketts expressed his confidence in Cubs’ General Manager Jim Hendry.

When asked if Jim Hendry’s job was safe, Ricketts replied, “I have 100 percent confidence in Jim. He’s working very hard to do everything he can to get this season back where we want it to be.”

Simple. Just a touch evasive. Businesslike.

Confidence – a complete belief in the powers, trustworthiness, or reliability of a person or thing – is one of those buzz words owners and front office types like to throw around. And, if they used it properly, we probably wouldn’t have the expression, “the dreaded vote of confidence.”

So, when Tom Ricketts uses the word confidence, you’ll understand if I’m usually unmoved. If he says he’s confident that the team will turn it around this year, or that the fans will flock back to Wrigley as soon as the weather is better, I think he’s just doing some hip shot PR. If he says he’s confident that the organization can field a winner in 2012, I think he’s just being optimistic in a carefully-phrased way. Those are expressions of confidence that can safely breeze by my ears without much thought taking place in the space between.

But when he said he has “100 percent confidence” in Jim Hendry, the hamster wheel in that space starts turning. And, after a few revolutions of the wheel last night, I liked what I was hearing.

I know what you’re thinking. You’re thinking I’m crazy, and wondering how could I be happy about Ricketts saying he’s standing behind a guy I’ve suggested letting go. I liked what I was hearing because Ricketts’ statement of confidence wasn’t about expressing a complete belief in the powers, trustworthiness, or reliability of Jim Hendry as the Cubs’ GM.

It was about managing our expectations.

Any good businessman knows that the best way to exceed expectations is to ensure that your stakeholders’ expectations are appropriately calibrated in the first place. Indeed, if you can get those expectations nice and low, it’s even easier (I’m looking at you, Apple revenue guidance).

Historically, Chicago Cubs fans have had low expectations – there was no need to artificially deflate them. But with the we-can-almost-taste-it year in 2003, and the subsequent uptick in spending, our expectations rose. Perhaps unreasonably.

And nowhere did they raise more precipitously than with respect to the performance of individual players and management.

Key error in the fourth game of the season? Trade him.

Walked a guy with the bases loaded? Release him.

Haven’t won a game in a week? Fire the manager and the GM.

We’ve come to expect not only success, but, in the face of failure, we also expect immediacy. I think our expectations in that regard have probably grown too high. And Tom Ricketts, the successful businessman, was helping bring them back down.

Even those of us who’ve hoped the Cubs would part ways with Jim Hendry before this year’s trade deadline have to acknowledge that, from a logistical standpoint, it would be very difficult. First, the Cubs would have to find a suitable replacement who isn’t already under contract with another team or whose team wouldn’t mind the Cubs doing some pilfering (legitimate, in-house candidates to take over as GM in anything but an interim role are about nil). Second, the Cubs would have to come to terms with that replacement in a matter of days. Third, that replacement would have to get up to speed with the entirety of the Cubs’ organization – from the big team to the recent draftees – within a matter of weeks. Fourth, the replacement would have to actually put together good moves before the trade deadline, lest the whole exercise probably be more harmful than just riding Jim Hendry out for the rest of the year.

Based on Ricketts’ carefully chosen words, I think he gets this. I think he understands that he can’t count on making a front office change midseason. I think he also understands that he can’t avoid the media and these questions forever (his two-week silence already felt like half of a forever). So he did what any good businessman would do: he managed our expectations by letting us know that, for now, things can’t be changed. Moreover, he preemptively saved face.

Like it or not, doing his best to ensure that the fans are still on his side, however things play out, is not just good for Tom Ricketts, it’s good for the Cubs. An owner whom the fans hate is a dangerous thing. An owner whom the fans love is, himself, an even stronger fan.

Don’t get me wrong: I don’t believe the best outcome is Jim Hendry sticking around for the rest of this season, let alone 2012. But if my *expectation* that Hendry could be gone as soon as July is unrealistic, I need someone in charge to tell me that I’m nuts. I think that’s exactly what Tom Ricketts was doing last night, while simultaneously hedging his bets in case he can’t find a better option (in his mind) for 2012, AND simultaneously refusing to commit to Jim Hendry in 2012 (“We’re just going forward right now [with respect to Hendry’s position], and I’ll see what the offseason looks like then. I’m pretty happy.”).

That kind of carefully choreographed dance is the stuff of Baryshnikov or Fred Astair. Or a really good businessman.

Besides, what was he supposed to say when asked if Jim Hendry’s job is safe? “Actually, no. We’re looking around, but it’s pretty hard to find mid-season the kind of top-shelf GM this organization deserves, so I’m not sure if I’m going to be able to fire him until after the season. I’d prefer to make the move now, but don’t be mad at me if it’s just not practical.”

Come on. He said what any owner, confronted with that kind of question, would say – and he said it in a carefully-wrapped package that left himself a dozen outs, while managing fans’ expectations for the immediate future. Do I really have to underscore the fact that he followed up his statement of confidence in Jim Hendry with the notation that Hendry is “working very hard” to get “this season” back where we want it to be? And that the team is “just going forward right now” with Hendry, and will “see what the offseason looks like.” Translation: I know this season has been shit, and I’m letting Hendry continue to work it out because I don’t have any other options right now. But this season is the the most to which I’m committing.

I thought, even as someone who would prefer Hendry were let go sooner rather than later, Ricketts’ approach was impressive. Were I one of his shareholders, I’d feel much better about the direction of the company today than I did yesterday.

So, in the end, I have 100 percent confidence in Tom Ricketts as a businessman. And better, I’m starting to have more confidence that he will translate his business skills to his role as the owner of the Cubs in a way that actually improves the team from the fans’ perspective, not just the bottom line.

Or maybe my expectations are simply getting out of whack.