Bring in the Experts: 5 Signs It’s Time to Make Outside Executive Hires

Founders are a restless bunch, especially in the tech sector. It’s rare to see a founder stick in the same day-to-day management role at the same company for one decade, let alone two or three. They’re much more likely to hire talented outside executives to scale their vision.

When they step aside is just as important as whether. Leave too early and you risk a jarring transition that strangles upward momentum in the cradle. Stick around too long and you risk outliving your skill set.

Watch for any of these five warning signs that it’s time to hire outside leadership talent and delegate some or all of your decision-making activities to others.

  1. You No Longer Have Time to Be Proactive

Founders and executives shouldn’t measure their value by the clutter on their daily calendars. If you’re booked solid for weeks into the future, you don’t have the capacity to deal proactively with emerging threats to your growth strategy. Depending on the nature of your obligations, you might not even have the flexibility to step outside your schedule and deal with more urgent matters.

Bottom line: if you’re not accessible and available to your team, hire a competent outside executive to handle some of your portfolio.


  1. You’re Not Getting Objective Advice

Are you surrounded by yes-people? That’s a common problem for first-time founders, whose early hires are just as likely to be devoted associates as subject matter experts.

“Get consistent reports from your management team in a timely fashion. Be proponent and encourage them to provide open feedback,” says entrepreneur George Otte, from Miami company Otte Polo Group. “Strategizing with your team will not only promote fresh ideas but will create a sense of commitment.”

  1. You Need Help Spotting Problems or Areas for Improvement

“Sometimes executives and business leaders may be blind to areas within their organizations that aren’t functioning optimally, or opportunities to enhance their business both externally and internally,” writes management consultant Breanna Bremer. “Consultants bring the fresh, objective perspective that can open up new ideas and avenues that weren’t identified previously, and enhance a business.”

Bremer’s statement applies to management consultants and business coaches specifically, but it’s no stretch to extend it to temporary or permanent executive hires more generally. If you’ve come to doubt your ability to spot current or future threats to growth, it’s time to bring in someone who can.

  1. You’re No Longer Attracting the Best

Talent begets talent. If your company is no longer attracting top-tier candidates, it’s likely because those candidates don’t regard it as a suitable place to launch or further a career. A well-publicized, high-wattage executive hire can flip that paradigm in a heartbeat.

  1. You’re No Longer Passionate About Your Work

Hey, founders are restless. There’s no shame in admitting that you no longer feel the same passion for your work as when you started. You’ll go on to better things — perhaps a brand-new venture. And, as long as you make the right external hires at the right times, the organization you built will continue on in good hands.

Author: Guest author

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