Five Questions With: Rachel Stephenson Sheff, Interim CEO at I.G. Advisors

How do you lead with clarity in a world that won’t sit still?

For Rachel Stephenson Sheff, it’s less about finding the answer and more about asking that question often, especially when the stakes are high and the room gets quiet.

Rachel is a strategist, CEO, and creative thinker. She co-created Young-ish and champions purpose-driven leadership. For over 15 years, Rachel has advised some of the world’s most influential organizations, from B Lab and the Obama Foundation to global philanthropies and fast-growing startups. Today, she leads I.G. Advisors, a social impact strategy consultancy, and plays a key role in shaping the next generation of leaders through the 100x Impact Accelerator and I.G.’s Leadership Lab.

But her approach isn’t about chasing scale for scale’s sake. It’s about staying grounded in people, cutting through complexity, and asking better questions.

In this interview, Rachel shares what makes strategy effective in the social impact space, why she believes generalists are having a renaissance, and what it means to lead with both vision and accountability.

Your work spans impact, business, philanthropy, and leadership development. How do you remain grounded in purpose while navigating such complex and evolving systems?

I’ve always worked with and for purpose-driven organizations and businesses, and one thing I’ve learned is that mission alone isn’t enough to sustain me. Where I really feel purpose – and what I really feel accountable to – is people.

It’s not that I’m not passionate about the bigger picture – I am. I care deeply about the world and feel lucky to have a career that keeps me connected to social and environmental progress. At the same time, the excellent people I get to work with undoubtedly give me the most fulfillment, joy and purpose. I feel an immense sense of responsibility to my team, board, clients and partners, and I’m grateful for that tether. 

I say this because bringing everything back to people, which everything can ultimately be brought back to, makes navigating different industries, systems, and perspectives a lot easier and more interesting. Common sense, strategic thinking, and the ability to build strong relationships are all you need.

You’ve led strategy for some of the most influential organizations in the world. What does an effective strategy actually look like in the social impact space, and where do you see leaders get stuck most often?

There are three things:

1) A good strategy is Impactful, Feasible and Fundable. All three legs of this stool are equally essential, and many organizations struggle with prioritizing them. They overly attach to historical programmes where impact is questionable, they limit feasibility to the current state of their team, or they pursue ideas with no sustainability baked in.

2) Your job is to hold the bigger picture, not drown in the detail. Sometimes, almost as a gesture of respect to the complexity of a cause, organizations don’t operate as clearly and audaciously as they should. You need to be able to explain your strategy in three short, sharp bullet points to anyone in 30 seconds. Your vision also needs to be visionary (!), i.e. it should expand our imagination.

3) As they say, “culture eats strategy for breakfast” – but, going upstream, leadership eats culture for lunch. Practically speaking, in every strategy you should name, in detail, the behaviours required to execute it, and then ask: are those behaviours encouraged, incentivized and modelled? A classic example is a strategy that requires speed and agility in an organization that prioritizes process and participation. There is tension there that’s not often explored. 

You’ve described yourself as a generalist with a creative edge and commercial sensibility. How has that interdisciplinary lens shaped your career, and why do you think it’s so valuable right now?

I’ve always been a generalist. In school, I was just as good at math as I was at English, and I liked them both for different reasons. I studied musical theatre at NYU and now run a strategy and management consultancy (which is not as different as you might think; consulting is performance, minus the tap dancing). 

I’ve always found my ‘generalism’ and interdisciplinary lens to be an asset, not a liability. Being interested in many things and connected to the zeitgeist on many fronts only strengthens and expands your worldview. Also, being good (or good enough) at many different kinds of tasks makes you better at managing across functions.

One question I get a lot is how to craft a career as a generalist – if you can do anything, where do you start? My answer is to think realistically about the life you want and what paths will get you there, and then to follow your curiosity and focus on relationships. Working with excellent people to create meaningful things is a wonderful way to build a career and live a life. 

Through your work with the 100x Impact Accelerator and I.G.’s Leadership Lab, you’re helping grow the next generation of impact leaders. What qualities do you believe are most urgent, and most underestimated, for this generation to cultivate?

Strong leadership is essential for anyone at any stage of their career, not just those with fancy titles. A lot of it boils down to a blend of visionary thinking, business acumen and emotional intelligence – an unbeatable and self-regulating combo.

First and foremost, you need to know yourself intimately – what you’re good at, what you’re not so good at, and what you need to succeed. Then, of course, you need to be able to ask for this support, even when it feels ‘silly’.

You need to know the difference between your anxiety and your intuition, and you need to stay out of drama triangles. You need to balance authenticity and vulnerability with professionalism and appropriateness. You’re the pilot flying the plane, and if there’s turbulence, no one wants to hear the panic in your voice. 

You also need to learn the skill of influencing, which requires a precise understanding of the system you’re operating in, the right relationships and the right tactics. 

Finally, you need to have whip-smart, clear communication. You need to be able to tell a story and pitch like a TED Talker. You need a 30-second version of your message, and a five-minute version where you double-click to expand on the same core structure.

There’s so much more I could say, but in summary, there are enough challenges out there in the world to deal with; your job as a leader is to get out of your own way and make sure you’re not one of them. 

You’ve built a career out of asking powerful questions, challenging assumptions, and helping others lead with clarity. What’s one question you return to often in your own leadership journey?

Something I ask myself all the time is: What is the best, most strategic use of my time and energy right now? What do I need? What does the business need?

It’s easy to distract ourselves in the safety of ‘busy’ work. But as CEO, the buck stops with you – there’s nowhere to hide and no excuses to be made. There are very clear measures of success for the business that I’m accountable to. Full stop. That accountability drives me every day.

It’s funny, in this year as CEO, I’ve never worked harder, and yet I’ve also never prioritized sleep, exercise and joy more. Because it’s not just about me anymore. I have a team of people depending on my performance for their livelihoods. My personal life is directly relevant to that equation, not just in terms of rest, but also in doing things that make me feel fully alive.

I used to wear burnout like a badge of honour. But since taking on leadership roles, and certainly since this CEO position, I’ve realized how deeply untrue (and dare I say immature) that is. No matter how systemic the problems are, as a leader, it’s still all on you. You have to find your agency.

Ironically, stepping into the highest-pressure role of my career to date has made me take rest and fun much more seriously. Who knew?