Keep Searching Until You Find Your Grant

Few leadership decisions create more excitement than hiring someone you believe will transform your organization, but it doesn’t always work out.

Few create more disappointment than realizing six months later that you were wrong.

Most leaders and owners have experienced both. Abraham Lincoln is a textbook example of this.

We spend countless hours reviewing resumes, conducting interviews, checking references, and evaluating candidates. We convince ourselves we’ve found the right person. Sometimes we have. Sometimes we haven’t.

That’s why one of my favorite chapters in Donald T. Phillips’ outstanding book Lincoln on Leadership is titled “Keep Searching Until You Find Your Grant.”

While the chapter focuses on Abraham Lincoln’s search for the right military leader during the Civil War, the lesson extends far beyond military history. It speaks directly to one of the most difficult challenges every leader faces: finding the right people and surrounding yourself with talent capable of helping the organization succeed.

Over the years, I’ve watched hundreds of business owners wrestle with this challenge. Some have made hires that transformed their companies. Others have made hiring decisions they later regretted. Most have experienced both.

What I’ve learned is that great leaders aren’t necessarily better at avoiding hiring mistakes.

They’re better at learning from them.

Why Hiring Is So Hard

One reason hiring is so difficult is that people are complicated.

As leaders, we’re trying to predict future performance using a limited amount of information. We interview candidates, review resumes, check references, and administer assessments, but at the end of the day we’re still making an educated prediction about how someone will perform in a future environment.

The candidate is making assumptions about your company.

You’re making assumptions about the candidate.

Both sides are attempting to forecast a future neither can fully see.

Unlike a financial decision or an operational decision, people decisions often take months before you know whether you were right.

Sometimes a candidate who impresses everyone during the interview process struggles once they’re in the role.

Sometimes someone who appears merely solid becomes one of your strongest contributors.

That’s the challenge.

People aren’t spreadsheets.

They’re complex, dynamic, and constantly evolving.

The Danger of Hiring from Desperation

Unfortunately, leaders often make an already difficult process even harder.

A key employee leaves unexpectedly.

Business grows faster than anticipated.

Customers demand more attention.

The team becomes overloaded.

Pressure builds.

Suddenly, the search shifts from finding the right person to finding someone who can provide immediate relief.

That’s when trouble begins.

When urgency takes over, standards often begin to decline. Concerns that would normally raise questions get rationalized away. Leaders start convincing themselves that weaknesses can be coached, managed, or ignored because the pain of leaving the position open feels worse.

But desperation rarely improves judgment.

In fact, some of the most expensive hiring mistakes I’ve seen were made by leaders who knew they were compromising but convinced themselves they had no choice.

The reality is that they did have a choice.

They simply didn’t like the alternatives.

Get Clear Before You Start Looking

One of the best ways to improve your odds is to become crystal clear about what success actually looks like.

Many organizations begin recruiting before they have fully defined the role.

They know they need help, but they haven’t carefully thought through what kind of person is most likely to succeed.

The best hiring decisions go far beyond technical qualifications.

They consider:

• Values
• Behaviors
• Personality
• Leadership style
• Communication style
• Motivation
• Learning agility
• Cultural fit
• Experience operating at your company’s stage of growth

I often encourage leaders to build a complete profile of their ideal candidate before beginning the search.

Not just what they will do.

But who they need to be.

What strengths are essential?

What weaknesses are acceptable?

What behaviors are non-negotiable?

What attributes separate average performance from exceptional performance?

The clearer you become about success, the more likely you are to recognize it when it appears.

The Mystery of Fit

Even when you’ve done all of this well, there remains a reality every experienced leader eventually discovers.

Fit is hard.

In fact, fit may be the most difficult part of the entire hiring process.

I’ve seen CEOs create tremendous value in one organization and struggle in another.

I’ve watched COOs thrive in one company and fail in a nearly identical company operating in the same industry.

I’ve seen executives leave one organization under a cloud of disappointment only to become stars somewhere else.

Why?

Because success is highly contextual.

The right leader for one organization may be completely wrong for another.

The right leader for one stage of growth may be wrong for the next.

The right leader for today’s challenges may not be the right leader for tomorrow’s opportunities.

Culture matters.

Team dynamics matter.

Leadership styles matter.

Organizational maturity matters.

Values matter.

Timing matters.

When all those factors align, success can seem almost effortless.

When they don’t, even talented people can struggle.

Understanding this should make us humble.

It should also keep us from being unnecessarily harsh on ourselves.

Many business owners assume every hiring mistake was obvious and avoidable. The reality is that there is a degree of uncertainty built into every people decision.

That doesn’t excuse poor hiring practices.

But it should remind us that hiring is difficult because people are difficult.

The goal isn’t perfection.

The goal is improving your odds.

Keep searching until you find your Grant.

Recruiting Is Not an Event

Another mistake many leaders make is treating recruiting as something they do only when a position becomes vacant.

By then, you’re already behind.

Talent doesn’t become available according to your schedule.

One of the questions I often ask business owners is simple:

“If your best employee resigned tomorrow, who would you call?”

Most don’t have an answer.

That’s not a hiring problem.

That’s a recruiting problem.

The most successful leaders I know are always recruiting.

They are constantly building relationships.

Constantly networking.

Constantly asking for referrals.

Constantly meeting people who may become valuable contributors someday.

They understand that recruiting isn’t an event.

It’s a process.

Just as great sales organizations maintain a pipeline of future customers, great organizations maintain a pipeline of future talent.

The best hires often come from relationships that were built long before the opening existed.

When You Make a Mistake

Despite your best efforts, mistakes will happen.

Every leader eventually hires someone who isn’t the right fit.

What I’ve found interesting is how often leaders struggle to acknowledge what is already obvious.

In my Vistage groups, I can’t tell you how many times I’ve watched a member spend six months trying to convince themselves a hiring decision was working when everyone around them already knew it wasn’t.

The employee knew.

Their peers knew.

The leadership team knew.

The owner was often the last person willing to admit it.

Why?

Because nobody likes admitting they made a mistake.

Unfortunately, delaying the decision rarely improves the outcome.

Strong leaders acknowledge reality.

They address issues honestly.

They learn from the experience.

Then they move forward.

What damages organizations isn’t making a hiring mistake.

What damages organizations is refusing to recognize one.

Hope is not a talent strategy.

The Cost of Settling

The greatest hiring danger isn’t making a mistake.

It’s knowingly settling for less than what the role requires because you’re tired of searching.

Every leader eventually reaches this moment.

The position has been open for months.

The workload continues to grow.

The team is feeling the pressure.

You’ve interviewed candidate after candidate.

Then someone appears who seems “good enough.”

That’s often the most dangerous moment in the entire process.

Because settling feels reasonable.

It feels practical.

It feels efficient.

But it rarely is.

The wrong person doesn’t eliminate the problem.

They often become the problem.

I’ve also seen the opposite happen. A leader stays disciplined, keeps recruiting, refuses to settle, and eventually finds someone who transforms an entire department. Those moments remind us why the search is worth it.

Looking back, I’ve never heard a business owner tell me they regretted holding out for a better candidate.

I have heard plenty tell me they regretted settling.

The difference between those two decisions often shows up for years afterwards.

Keep searching until you find your Grant.

Lincoln’s Search for Grant

Abraham Lincoln understood this lesson better than perhaps any leader in American history.

Before Grant, Lincoln endured years of frustration.

General McClellan possessed talent but lacked urgency.

Other generals hesitated when opportunities appeared.

Some blamed circumstances.

Some blamed resources.

Some blamed everyone except themselves.

Repeatedly, Lincoln found himself confronting the same question leaders still ask today:

“Why can’t I find the right person for this job?”

The stakes could not have been higher.

His decisions affected the future of the nation and the lives of hundreds of thousands of people.

Yet Lincoln never stopped searching.

He never convinced himself that mediocrity was acceptable.

He never lowered his expectations because the search had become difficult.

He continued evaluating.

He continued learning.

He continued looking.

Eventually, he found Ulysses S. Grant.

What’s fascinating is that Grant wasn’t necessarily the best general Lincoln could have imagined.

He was the right general for the challenge Lincoln faced at that moment. He proactively fought and won battles.

Grant possessed the determination, resilience, aggressiveness, and strategic mindset the Union desperately needed.

Most importantly, Lincoln recognized it when he saw it.

Once Grant took command and began building his own leadership team, the effectiveness of the Union Army improved dramatically.

Less than a year later, the war was over.

Lincoln’s greatness wasn’t that he found Grant immediately.

His greatness was that he refused to stop looking for him.

Keep Searching Until You Find Your Grant

The real lesson from Lincoln isn’t about hiring.

It’s about resilience.

Leadership requires the ability to endure disappointment without lowering standards.

It requires the humility to admit mistakes.

It requires the discipline to keep searching when the process becomes frustrating.

And it requires confidence that the right person is worth waiting for.

Lincoln’s story reminds us that finding great talent is rarely a straight line.

There will be disappointments.

There will be false starts.

There will be candidates who look perfect and prove otherwise.

There will be times when you’re tempted to lower your standards simply to end the search.

Don’t.

Stay clear about what you’re looking for.

Stay disciplined in your process.

Learn from your mistakes.

Correct them quickly.

And keep searching.

Because somewhere out there is the person your organization needs next.

Keep searching until you find your Grant.

Once you find him or her, it will be more than worth the effort