To Succeed in Executive Leadership, Burn the Playbook

There’s a special type of deep shame that festers when you’ve been passed over seven years running for a promotion that is the gateway to executive leadership roles.

I know the ache and misery of these doubts because of my former 13-year career at a financial services regulator where I spent half my time pursuing a senior management role only to be met with moving goalposts, a gut renovation of the career management process, and exhortations to take lateral roles to become “more well rounded”.

If my C-suite transition could happen, the lessons are relevant for your story too

Fate fortunately intervened and I was tapped for an executive leadership role at a portfolio company of one of the most powerful private equity firms in the world. While I fully acknowledge the luck involved in this opportunity, I am confident that my story is replicable for others because:

1)The odds of me making this leap were literally non-existent because I grew up at the poverty line, my parents never worked in the US, I had no industry connections, and I was working at a government agency at the time that I was tapped

2)I had been preparing over the course of those seven years to capitalize on such a stroke of fortune

What to do when you're stuck in an individual contributor position

1. Define and accept what you consider to be your good enough effort

2. Work with an executive coach

3. Build the systems that will sustain your family life

4. Be patient and pursue the projects that matter to you at work

You’re never stuck as long as you remember that you are in control of the hours you don’t need to use on work itself. The goal in any job is to become so good at what you do that your efficiency allows you to flex your time in other more meaningful ways. You’re being paid not for how quickly you do a job but for the amount of time you invested to achieve that level of speed and your ability to connect the dots for any situation.

Recognizing that I had achieved maximum efficiency and subject matter expertise but would not be rewarded anymore was the first step in my ability to make the leap to an executive leader role.

Following this epiphany, I deliberately dropped into a biding time posture. I decided that building the educational and developmental foundation I wanted for my son would be my north star. Private school was out of reach so I made sure that I delivered a world-class education to him.

What gave me the confidence to lean into family life was that I knew I was a highly qualified candidate. While I interviewed just 3-4 times a year, I sought feedback from every failed final round interview.

When I didn’t clinch a desired international secondment at the Bank of International Settlements in Switzerland, I was crushed then elated when the hiring manager inadvertently shared with me that I had come in second in a global pool of applicants. This is the closest I have come to winning a Miss Universe pageant and to this day, this is a silent achievement that I pat myself on the back for - even if it’s not a bullet point to add to a resume.

This quiet win buoyed me and I doubled down on bolstering my career. I pursued certification to deliver design thinking training. I dove deep into quiz land - Myers- Briggs, DISC, CliftonStrengths Assessment - and discovered that there truly is an art to developing a good career test.

I also hired an executive coach to level up my executive presence and get reps on interview prep. I love my executive coach and count her as one of the best investments I've made in myself. I still work with her to this day and recommend a coach to anyone seeking new roles or transitioning into a new one.

Despite all this, one of the last roles I interviewed for was offered to an external candidate. At this point, I was in year 11 of 13 of my career at the regulatory agency. I cast my anchor away and built Buoyant Bloomer, an educational consultancy focused on teaching parents how to deliver a world-class education even if their kids were in public schools. I kept chugging along at work and one fine day in year 12, the kind of never before done project that I had built a reputation for knocking out of the park landed my way.

For that year, I lived and breathed deposits. I went on to conduct the first ever review of that kind of firm. 16 months later, I was hired as the firm’s Head of Regulatory Relations.

How I Made the Leap from Individual Contributor to Head of Regulatory Affairs

So this is where I tell you I rode off into the sunset right? Well, this is where I tell you of all the things I quickly had to learn.

●Salary negotiation: The three times in my life when I started over at a new workplace coincided with entry level and recent graduate roles. I had never actually had the chance to ask for my worth because these pathways define your value for you. Of all the prep I did to land the executive leadership role, paying the salary coach was the best thing I did. Don’t fall for the ones that take a percentage of your first year’s salary.

●Mindset revamp: After negotiating a package I was proud of, I knew I needed to work on my money story and the mental story I told myself about my worth and my abilities. Having survived 13 years of being gaslit, being told I wasn’t good enough, having to over-prove myself to no success, I had to confront the compensatory controls I had put in place to survive a work environment that was toxic. This was free but took months of work to untangle.

●The new rules of time management - block off two hours of your day to get shit done. Of all the hacks and tricks shared by luminaries like Laura Vanderkam and Oliver Burkeman, this was the one thing that made a positive difference in me surviving the first year as an executive.

I can’t stress the importance of negotiating the latest start date you can give yourself, especially if you’ve spent more than a decade at one company.

I also put into place systems to manage our family life which I won't go into detail here. However, the heavy lifting I put into place on this front was singlehandedly the most important thinking and effort that I expended. It means that even when I'm pulling 8-10 weeks of 100-hour weeks, our family life does not take a backseat with those systems in place.

I'm closing in on two years in my new role and I wouldn't trade my old life for the one I have now. I am firing on all cylinders and so thrilled to be playing big the way Tara Mohr wants us to. Having lived for so long in the shadows, I am grateful for how far I've come and so ashamed that I accepted so little for so long! Bon Courage my fellow kindred spirits - the big life beckons and I am here to tell you that it should not be feared but embraced!