THE WORKPLACE WIRE
BRAVELY / HUMAN COACHING + AI / BEA JOINS MEETINGS WITH PERMISSION / COACHING IN 33 LANGUAGES

Company / The art of the awkward conversation

Bravely: rehearse the conversation that could change your job

The difficult conversation is a workplace skill with remarkably little rehearsal time. Bravely sells employers a place for that rehearsal - and is now bringing an AI coach into the meeting itself.

In 2019, Sarah Sheehan found herself back on the phone. A Bravely coach had fallen ill minutes before a session, and the co-founder volunteered to cover. She had been the company’s first coach; building the business had pulled her away. Now an employee was telling her they had been judged a poor leader and were considering stepping back.

The ending was inconvenient for anyone selling a tidy success story. The employee did decide to step back, Sheehan wrote, for their well-being. Progress had taken a direction an employer might not have predicted. That small episode captures Bravely’s central bargain: a company pays for support, while the person receiving it needs room to arrive at an answer of their own.

  • The offer: confidential professional coaching paid for by employers.
  • The audience: employees, managers and executives, with different levels of support.
  • The new chapter: Bea, an AI coach that joins meetings with permission.

A rehearsal room without the office politics

Founded in 2017 by Sheehan and Toby Hervey, Bravely began with a gap its founders had felt themselves: workplace situations in which existing support did not help them move forward. An early investor described the service as off-the-record conflict coaching. The opportunity was broader than conflict, but the awkward conversation was an excellent place to start.

A performance review, a disagreement with a colleague, a request for more responsibility: each demands judgment as well as vocabulary. Friends may sympathize. Managers have their own stake in the outcome. Bravely offers an outside professional who can help someone examine the situation, consider options and prepare the next step. An employer gets another channel of support; an employee gets space to think.

According to its employee FAQ, sessions can last up to 45 minutes and happen by audio or video. Coaching is available in 33 languages. The network includes certified coaches and HR veterans, trained in Bravely’s methodology. Participants can return to a previous coach or try someone new. Employers determine session allowances, so access depends on the program purchased.

“Sometimes the best way to see the big picture is to put yourself back on the front line.”Sarah Sheehan, reflecting on her return to coaching, 2019

What employees wanted surprised the buyer

Autodesk’s experience supplies a useful correction to the idea that coaching is chiefly for people in distress. Its May 2022 customer story describes a company pursuing cultural change, with coaching initially offered to half the workforce and then extended to everyone. The support complemented managers rather than requiring them to conduct every difficult conversation themselves.

Leadership found something unexpected in the reports: employees were discussing careers, rather than simply stress. The distinction matters. Someone seeking a coach may be ambitious, uncertain about their next move, or trying to become more effective. If the invitation sounds like remedial treatment, those people may never accept it. Autodesk’s experience suggests making development an ordinary resource, available before a problem becomes conspicuous.

At BrainPOP, the bottleneck was time. Its small HR team wanted to give employees individual attention during the pandemic and could not supply enough of it. Executive coaching covered too narrow a population; wellness-only services did not address the whole career question. BrainPOP introduced Bravely in September 2020.

BrainPOP’s listening experiment
28%used at least one session
in the first nine months
Reported reluctance to speak with managers
Earlier quarter17%
Later quarter2%
Company-published 2021 case study. Observational results; they do not establish that coaching caused the change.

That participation figure is more useful than a vague promise of transformation. It shows people actually tried the benefit. The reported change in manager conversations is encouraging, too, though other changes inside BrainPOP could have contributed. A buyer can copy the measurement discipline: distinguish access from use, and use from evidence that work has improved.

Different doses of the same conversation

Bravely sells a portfolio rather than a single coaching schedule. Boost provides on-demand sessions for individual contributors and managers, with webinars and a content library. Advance turns the relationship into sustained leadership development: a skill assessment, a personalized plan, regular meetings and a final assessment. It advertises unlimited coaching and reports on both development and participation.

Exec addresses senior leaders through individually matched coaches. Bravely’s homepage describes a 12-month engagement with unlimited sessions and flexible cadence. The executive product page emphasizes leadership experience and professional credentials. Workshops add group learning alongside individual coaching. The practical choice is between help with a present situation and a longer relationship designed to build particular skills.

Bravely coach Adewale Bello smiling in glasses and a jacket
Adewale Bello, one of Bravely’s coaches. Behind the platform, a person who has spent time on both sides of the manager’s desk.

The employer is the customer, with HR and learning teams the natural buyers. Bravely’s commercial pages lead to a demo. Its August 2021 Series A brought $15 million, led by Telescope Partners; the company then reported fourfold business growth over the preceding year. Those figures describe investment and historical momentum, rather than what a customer’s program will cost.

Now the rehearsal room can attend the meeting

Bea takes the proposition into a different setting. Bravely says its AI coach can join a meeting with permission, offer a reflection afterward and deliver coaching through workplace messaging or its web app. Over time, recurring signals become patterns. Users can also rehearse a conversation, examine a decision or discuss what happened afterward.

The product’s promise rests on context: speaking to your own team and presenting to senior leadership are different situations. Bravely says individual reflections remain private, while anonymized organizational insights require a minimum group size. Its human-coaching FAQ also describes confidentiality exceptions, including imminent harm. Trust needs that level of specificity when the employer is paying.

Bravely competes with BetterUp, CoachHub and independent coaches. Both large platform rivals offer human and AI coaching, so neither technology nor broader access settles the comparison. Bravely’s case is clearest in its emphasis on everyday workplace moments. For a reader, the useful habit is modest: choose one conversation, rehearse it, act, then review what happened. Coaching needs an opportunity to practice and an organization willing to listen. No amount of rehearsal can make an employer keep a promise it has decided to break.

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