Forcing the Hand (Career Progression by Ultimatum)
Ask for more, give them 60 days, and if nothing comes back — go get it elsewhere.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 6
- Confidence
- 82%
Through her 30s Bova changed jobs roughly every 18 months, at a time when that read as high-risk rather than normal. The method was consistent: as a quota-bearing rep consistently hitting number, she'd tell her leadership she loved the work but wanted more responsibility and to move up. She'd get the obligatory 'we value you, nothing right now, give us 60 days,' accept the timebox, keep performing, and return at the deadline. There was never an opportunity. So she'd leave — and each move increased her base pay (nearly doubling her income over the run), her title, and her sphere of responsibility. The deeper payoff was lateral: she moved from sales to leading marketing teams to customer service teams, gaining a complete view of every customer-facing function. Part of the same method is honestly assessing your type — she concluded she was risk-averse and an intrapreneur, not an entrepreneur.
Origin
Bova spent her 30s as an individual quota-bearing sales rep in early web technology, changing jobs every 18 months when three changes in three years still drew 'what's wrong with you?' Each cycle followed the same ask-wait-leave pattern, ending with her running a $300M business inside a Fortune 500.
Core principles
- 01Earn the right to ask by consistently hitting your number first.
- 02Ask explicitly for more responsibility rather than waiting to be noticed.
- 03Give a defined window, then hold them to it.
- 04Silence at the deadline is the answer — treat it as data, not rejection.
- 05Lateral and downward moves that broaden your view can outperform a straight ladder climb.
- 06Not everyone is meant to be an entrepreneur; intrapreneur is a legitimate destination.
How to run it
- 1
Earn the standing
Be great at what you do and consistently hit your number. The ask only carries weight when your performance is not in question.
- 2
Make the specific ask
Tell leadership plainly: I love working here and I love what I'm doing, but I want more responsibility and I want to challenge myself. Name the role — team lead, sales manager, VP.
Pro tip Lead with genuine appreciation; this isn't a threat, it's a request.
- 3
Accept the timebox and keep performing
When they say 'we'd hate to lose you, give us 60 days,' say okay and take the 60 days. Keep doing your job at the same level throughout.
Watch out Downshifting during the window forfeits your leverage.
- 4
Return at the deadline
At the end of the window, sit down and ask what you've got to work with. Don't wait to be called — in Bova's experience, they never came back.
- 5
Force the hand
If there's nothing, decide: stay and hope you're a director in five years, or go force the hand elsewhere. Each move should raise base pay, title, and sphere of responsibility.
Pro tip Optimize for a complete view across functions — sales, then marketing, then service — not just the next rung.
Watch out Sometimes the right move is lateral or even down; trust the process.
- 6
Diagnose your type honestly
Talk it through with someone who knows the alternative path. Decide whether you're actually an entrepreneur or an intrapreneur — being risk-averse and wanting security is a valid answer, not a failure.
Pro tip A long honest conversation with a real entrepreneur beats a self-assessment.
Watch out Side-hustle culture pressures people into entrepreneurship they aren't cut out for.
In the wild
Through her 30s Bova repeatedly asked for more responsibility, got the 60-day promise, kept hitting quota, returned at the deadline to find nothing, and left. Along the way she moved from sales into leading marketing teams and then customer service teams.
→ Nearly doubled her income across the run, gained a complete view of every customer-facing role, and grew a $300M business inside a Fortune 500 company.
At dinner in Sydney with Naomi Simson — Shark Tank Australia investor and EY Entrepreneur of the Year — Simson spent the first bottle telling Bova she should go out on her own. By the end of the second, having genuinely talked it through, Simson concluded it wasn't for her.
→ Bova uncovered that she is risk-averse and values corporate security — confirming intrapreneur, not entrepreneur, as her path.
Common mistakes
Waiting to be noticed
Hoping that hitting quota alone earns a promotion means five years pass while nobody makes a plan for you. The ask has to be explicit.
Letting the timebox lapse
In Bova's experience, at the end of 60 days nobody ever came back. If you don't reconvene at the deadline, the window silently becomes another year.
Forcing yourself into entrepreneurship
Side-hustle culture tells everyone to start a business, and many fail because they aren't cut out for it. Being risk-averse and wanting security is a legitimate self-diagnosis, not a deficiency.
Is it for you?
Best for
High performers in corporate roles who want more responsibility and are hitting their targets already.
Not ideal for
Those not yet delivering consistently, or in markets where changing roles carries a serious stigma or visa risk.
From the transcript
“I forced the hand to say — am I going to stay at this business and hopefully five years from now I become a senior…”
“At the end of 60 days, lo and behold, I didn't hear from them.”
“I uncovered that I am risk adverse, that I like the security of corporate America.”
From the episode
Tiffani Bova: Growth Hacking Your Business
Tiffani Bova