Pressure Creates Diamonds But Also Bursts Pipes - How to Balance Driving the Management Team with Realistic Expectations
Written by Michael Frankel, Investor and Host of Skytop’s M&A Exchange / April 15, 2026
Michael Frankel is the Founder and Managing Director of Trajectory Capital, a private equity fund focused on B2B technology businesses. He is an innovation, strategy, and corporate development leader with senior roles across global technology, information services, and professional services organizations including VeriSign, LexisNexis, IRI, GE Capital, and Deloitte. At Deloitte, he led the New‑Venture Accelerator (DNA), guiding strategy and portfolio operations for emerging technology businesses that now generate more than $4B in new revenue.
He has built and scaled programs that open new markets, launch new offerings, and expand business models across technology, data, analytics, and services. In corporate development roles, Michael has overseen more than 100 M&A and strategic transactions totaling $10B in capital, along with 18 corporate venture investments that strengthened ecosystem partnerships and delivered strong returns.
As a growth operator, Michael has served in CFO, COO, and GM roles for high‑growth technology businesses, professionalizing operations across product, finance, marketing, HR, and legal. He has led multiple financing rounds, built executive teams, and executed restructuring initiatives that improved scale, margins, and revenue performance. At Deloitte, he also led portfolio‑wide operational support in pricing, sales enablement, product management, marketing, and executive recruitment.
Michael holds a BA, MA, JD, and MBA from the University of Chicago. He is a frequent speaker on innovation and corporate growth, the author of three books on M&A and strategic transactions and has served on public and private boards as well as the University of Chicago Alumni Board of Governors. He lives in the New York area with his wife and daughter.
Every board strives to deliver results for investors. However, private equity backed companies are under greater pressure to deliver change, growth and results in just 3-5 years. And most private equity investments are made with an expectation that the company will go through substantial change during that short investment period - whether growing and expanding, ramping up profitability or achieving an effective turnaround. As a result, private equity backed board members face a unique challenge: how to apply the right level of pressure and expectations to the management team to achieve attractive results quickly, while not setting expectations so great that management is doomed to fail to meet them - and knows it.
First you must reach alignment around the facts on the ground. Everyone must share the same view of the current state of the company and the market. If the board thinks there is no competition, and management thinks they are out there fighting dragons, you will never agree on a growth path. So you need to dig into not only the financials but customer expectations, addressable market, competitive landscape, evolving technologies and a myriad of other topics.
Once you are aligned around ‘what is’ you can turn to agreement about ‘what can be.’ I generally start by having management plant a flag with an initial cut at their plans for the business in 12-36 months. This is long enough to encompass more strategic plans like product evolution, but close enough in, to allow us to get fairly specific on metrics like spend and revenue and hiring and investment. Armed with this high level vision, management can construct a detailed budget and operating plan. The board can dissect and challenge the budget and plan before agreeing to it.
Finally, the board can monitor performance. To quote one great American, Mike Tyson, everyone has a plan until they get punched in the face. No multi-year plan ever holds completely true and over the next 12-36 months, the board and management will perform the complex dance of debating and adjusting the plan as reality - both good and bad - sets in.
The most effective board members take this journey with management from initial alignment to ongoing dialogue. They make sure that they are having a fact-based discussion with management, applying pressure that is reasonable and based on agreed-upon facts. They are careful to consider the situation from the point of view of management and ensure that they apply pressure in ways that are realistic and impersonal. That’s not to say cold, but rather frame their expectations around actions and results, and generally not based on personal attacks or judgements. There will be misses and failures. But a board member that has taken this journey with management will be in the best position to help guide the business applying pressure that is reasonable and well received by management.