I’ve been every animal there is when it comes to organizational change, from the charging bull in a china shop to the adaptable frog in boiling water. Upon starting my own company, I expected life as an entrepreneur would be different, with more appetite and capacity for constant change, since startups exist to disrupt.

Then came 2023.

We’re now halfway through, and it’s clear none of us will exit this year unscathed. Higher interest rates and Silicon Valley Bank’s collapse shook credit markets and ended the easy money. Artificial intelligence creates efficiency that might render our very livelihoods obsolete. Social media, once a justifiable mix of procrastination and customer acquisition, is a mess of new algorithms, toxic trolls, and entrants promising better. State legislatures are attacking LGBTQ+ rights as the Supreme Court rolls back affirmative action. And don’t forget the whiplash and confusing guidance on where to work: at home, in the office, or just don’t ask, don’t tell.

I need a minute.

I don’t have a minute.

To get through this year of uncertainty and urgency to pivot, I’ve found myself turning to a slew of lessons learned from past years of leading change-management efforts and—excuse the mega-cliche—building the plane while flying it. Hopefully my mistakes can save you some pain and make for a less bumpy ride.

Modulate your communication style.

I once worked with a leadership coach who asked me how to get to the subway from my house. “Take a right on 34th Avenue, walk down to 82nd Street, make a left, and you’ll see it.”

Her response: “Where’s 34th Avenue? When you say ‘down,’ do you mean south? How many steps before I turn left? How do I know I will see it when I don’t know what it looks like?”

This simple exercise didn’t just change how I give directions. It also prompted me to start tailoring the way I explain strategies or new initiatives, depending on my audience, and to completely overhaul how I run meetings. I used to hate PowerPoint (and honestly, still do), but I now understand more clearly that some people needed to see a list or a roadmap in order to take me seriously.

Don’t forget the why.

I used to curse the people who would constantly ask: “What is the problem we are trying to solve?’

In my head, it was always so clear. Our look and feel is from 1979. Our tech sucks. This organization borders on irrelevance. The problem we are trying to solve is that we have no future!

As problem statements, though, each of those thoughts was way too big and sweeping. Yet again, I learned to get more exact and precise in what we were trying to solve. The articulation often led to deeper collaboration, especially from those in the trenches, who could share their frustrations and potential ways to improve processes.

Bureaucrats are a needed force.

Change agents tend to embrace other change agents. Our new products and promotions attract other loud, extroverted people who pledge they are on board.

Aim elsewhere first. The people who make an organization run are often the bureaucrats—the ones whose roles and ways of working we might see as outdated, problematic, or expendable. If you can get them on board with your ideas, then you are golden.

This strategy also helps change feel possible from up and down the corporate ladder, not just dictated from above. Offering further incentive, a recent McKinsey report on the importance of middle managers concluded: “Organizations with top-performing managers yield multiple times the total shareholder returns (TSR) of those with average or below-average managers over a period of five years.”

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Find a North Star to rally around.

About a decade ago, a rising New York Times executive explained to me why the paper was so focused on a subscription strategy: not just to generate revenue, but to unite multiple departments around a common cause. Recently, a colleague of mine met with another Times executive who shared the same message. That discipline is not an accident. These big, unifying ideas can take years to trickle around, but they’re worth the investment.

I’ve thought about this a lot in the constant need to explain why constant change is necessary. Change for change’s sake feels like feeding the ego of the change agent. Chasing revenue is too vague and lacks purpose. I’ve learned to find a cause and then break up smaller parts of the why: “We should dominate in [x category]” or “We want users to come to our site more than once a day.”

Get okay with ambiguity.

Empower your people to trust their own judgment in the face of uncertainty. That starts with empowering them to trust their own judgment, full stop: An upcoming report commissioned by Kingsley Gate Partners and to be released July 17 finds a quarter of senior executives say they were not asked about their decision-making capabilities at the interview stage and only around a third (36%) say that their decision-making style aligns with that of their organization.

Knee-jerk resistance to change is understandable, especially if you haven’t felt supported to make calls without having all the information. People know what they know. But in order to create a culture of innovation, there needs to be comfort with ambiguity. That can be hard, especially for women and people of color, who might not have the safety nets or internal support networks to protect them if they fall—or fail.

Assuring people you have their back goes a long way in getting them comfortable with the ambiguity of change and experimentation. Culture Amp CEO Didier Elzinga explained in a blog post that a culture-first company is one that “builds trust through vulnerability and actively seeks out employee feedback.” That means that we cannot be arrogant in demanding change—or in predicting results.

You want people to embrace the new with the assurance that they are supported no matter what happens when they do. In another post, the company pointed to internal data indicating “that engagement highly correlates with innovative behaviors in all organizations … that encourages employees to innovate, even though success is not guaranteed.”

Recognize that change doesn’t only come from within.

For all the memos explaining what’s coming and why, sometimes the greatest motivator for employees is external. One reason I became active on social media is to call attention to the work of my colleagues and build a pulpit of positivity. I began writing for trade publications to showcase examples of innovation. Slowly, I began to hear those examples parroted back to me as a philosophy. I looked for opportunities for middle managers and staff to get exposure to new ideas through industry panels and conferences.

Highlighting or processing the wins outside of our teams helps us break down what works and the business values within that propel us. Arguably, it’s why I write this column: to hold myself accountable to the type of work culture I seek to continuously build, accepting the plane might never be fully completed nor the ride an especially smooth one.

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