The Bears are working their way through a mountain of interviews as the opening act of their coaching search.

They’ve got way more than anyone else on the hunt for a new head coach, in an attempt to survey the scene and make sure they exhaust their options in an attempt to get the hire right after several swings and misses at the head coach spot.

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That’s not all general manager Ryan Poles must do during this offseason, a massive one leading into a a 2025 campaign that president Kevin Warren deemed crucial for football operations and the team’s stadium push.

The Bears need some positive momentum in the worst way, and there’s a way to set the organization up for success in the coaching search and the hunt for roster upgrades. Here are five questions the Bears must answer leading into the next season.

Will Bears go big at head coach?

There are some bigger names involved in this hiring cycle, including individuals who have had success at other places. The Bears have only hired one head coach who previously had the title, and the John Fox experiment didn’t work out well.

Mike Vrabel and Pete Carroll are available to Chicago is they play their cards right. Ron Rivera is set to interview with the Bears as well, and he has a storied history with the franchise.

[Editor’s note: Vrabel has reportedly agreed to a multi-year deal to become the Patriots head coach]

Going big for Lions OC Ben Johnson is also a possibility, and someone who could pair well with quarterback Caleb Williams.

All of those guys will require big paychecks. Ownership must view this hire in the way Warren described the upcoming year. They can’t let cost be an issue. They’re interviewing tons of people for the opening, and some names in the group are less inspiring than others. Ending up with a consolation prize isn’t an option here, especially with only six vacancies available. It sure seems like Vrabel could be in New England and that Las Vegas is pushing hard for Ben Johnson. The Bears consider their opening as the most attractive on the market, but that isn’t worth a discount. Sometimes money talks, and they Bears need to be aggressive in a competitive market.

Can Bears find someone to develop Caleb Williams?

There’s no doubting Caleb Williams’ talent. He has it in droves, showing flashes of wow factor during an up-and-down season where he was clearly impacted by all the changes to the coaching staff. He often made spectacular plays but was inconsistent with the singles and doubles, an area where a no-gray-area coach could help make sure he takes small profits when available. He also needs a scheme that helps him make quick decisions and alleviates stress on him and his assignments in protection.

That doesn’t mean the Bears must go with an offensive-minded head coach. It does mean the offensive coordinator pick becomes paramount if the Bears end up with a CEO-style of coach. That’s an option for Poles, so that type of head coach had better have a top selection in mind. With some of the more experienced candidates, they’ve certainly got the connections to deliver on a top OC.

Can Ryan Poles fix the lines?

The Bears offensive line will look a lot different than it did in 2024. It’s entirely possible that there are four new members of that starting group, with right tackle Darnell Wright as the lone mainstay. While mock drafts often associate a top offensive tackle to the Bears at No. 10 overall, but Braxton Jones can perform well in that space. They need to revolutionize the interior line, where both guards Teven Jenkins and Matt Pryor and center Coleman Shelton are headed for unrestricted free agency. The Bears should spend big there and use an early round draft pick on that spot.

The Bears need a pass rusher, too, and the 10^th pick could be a spot to nab one to operate opposite Montez Sweat.

How will the Bears use significant salary-cap space?

The Bears have tons of money available to spend in free agency. Per OverTheCap, the Bears have $80 million in space heading into this offseason. They’ve got a quarterback on a rookie contract, so they can go big on an interior lineman or a pass rusher or safety.

The Bears are eligible to re-sign T.J. Edwards and slot cornerback Kyle Gordon, which would be smart to lock them up before they hit the open market after next season. Poles has the ability to make a splash in free agency, but must spend correctly to maximize value. The new head coach and the systems he installs will provide some insight into the skill sets required to fit in well as the Bears usher in a new era.

Will the Bears start stadium construction?

Bears president Kevin Warren has stated several times that he’ll put shovels in the ground on a new stadium at some point in 2025. That’s seems ambitious, considering they don’t yet have a site set. The Bears would prefer to build down by the lakefront, though there are some hurdles to clear before that site becomes truly viable, and there’s no guarantee that region will work out.

The Bears have “optionality,” Warren says, with property owned in Arlington Heights. The Bears have a clearer path there, but the push to remain in Chicago city limits hasn’t stopped. This is a big year for the stadium push, and the team must make tangible progress in their quest to build a new venue.