Know When to Hold Them and When to Fold Them

Nov 2, 2022 | Executive Coaching, Political Agility

As Grammy-award winning singer Kenny Rogers once explained, “You’ve got to know when to hold ‘em…know when to fold ‘em.” It’s pretty easy to manage your hand during penny ante games. There’s no pressure. But when salaries and careers are on the line, playing the trump card of ending a business connection becomes a complex decision.

At what point do you cut ties with people, personally or professionally?


High Demand, Low Connection

We see this dilemma with our senior-level executive coaching clients. They have people whom they barely knew in school want to connect on LinkedIn. The two have taken very divergent paths since graduation. My client holds a C-suite position. The classmate is between mid-level jobs. “College buddy” immediately launches into asking for career counseling, a job opportunity, or “a good word” to someone on their behalf. Forget establishing a relationship or building trust. Throw me a lifeline, now!

First of all, how can you vouch for someone when you have no idea of what their character has been for the past decade? Second, their unabashed comfort with seeking favors out of the blue has me questioning their character.

We encourage clients who feel besieged with networking requests to maintain strong boundaries. Don’t be haughty or rude, but don’t make yourself readily accessible either. Maybe send a note in reply to their message. That’s more than they would get from cold-calling people who didn’t graduate from the same university. But do not engage in a real-time conversation via phone, text, or messenger without a clear-cut purpose that would be mutually beneficial.

Remember, those networking to meet you – or gain access to your sphere of influence – perceive their connection to you differently than you. There may be great hopes pinned on adding you to their network. They’ve practiced their pitches. They know their playbook, and they are attached to the outcome.

You’re only barely attached to them. If at all. Stand your ground and enforce your professional boundaries.

Apropos to this season, leaves are detaching from trees all around my home in Minnesota. The tree does nothing but stand. It will outlast its foliage. Always has. Always will. Eventually gravity or wind will separate the leaves from the branches because they don’t have the wherewithal to hang on for more.

In the case of people who are only seeking a one-sided exchange and offer no reciprocal value to you, in due course, they’ll move on when it’s apparent that they’ll not get what they want out of you.



High Connection, Low Return

Sometimes we outgrow our peer group, friends, or team. One individual has their development plan, their coach, and they’re building skill sets to prepare themselves for a higher level of responsibility. Another may be quite capable, but they aren’t as driven to advance because their priorities are in areas other than climbing the ladder.

As the gap increases between these to co-workers, both will come to a point where they feel the need to self-select out of the relationship or accept that the dynamics are changing. As long as they derive some benefit from the bond – accountability, activities, emotional support – it’s good to maintain a friendship outside of the office. But if there’s no return on the relationship other than wistful pining over nostalgia and bitterness about how things have changed, it’s time to limit exposure to the negative person.

“But how?” you may ask.

Brené Brown said it best, “Clear is kind. Unclear is unkind. Stop avoiding the tough conversations because you think you’re being polite or kind to people.”

Just like you would with a direct report, give your troublesome friend the gift of feedback. “Your ‘x’ behavior causes this ‘y’ predicament. Please address it.”

If they’re not willing to take the feedback and act on it, you move on to the next tough conversation. “I don’t see you growing in this area. I wouldn’t be a good manager (or friend) to let this continue. For that reason, I’m giving you 60 days to find something different, and here are the kinds of roles that I will support you in your search.”

This is tough, but it’s actually nicer than kicking the can down the road until there is nothing left of the relationship to be salvaged. It requires unflinching honesty.

“Honesty is a very expensive gift. Don’t expect if from cheap people.”
~ Warren Buffett


Protecting Your (Bad) Hires

Sometimes you take a chance on hiring or promoting someone who ends up not holding up their end of the deal. Now you feel as though your decision is under attack each time that person’s performance comes under scrutiny.

Are you really being a champion for your new hire while they’re getting acclimated? Or are you protecting your own reputation?

This is where honesty mixed with humility comes into play. It’s time to say, “You know what? I got this one wrong.” And you must have the difficult conversation with your employee to explain their standing in the company. Put the onus squarely on yourself as the one who made the hiring decision, and let that person know that you’re making a change for purely professional reasons.


Who you choose to surround yourself matters. “You are the average of the five people you spend the most time with,” says Jim Rohn. Choose wisely. Take a lesson from the seasons. There comes a time to drop what no longer serves you well. If you assess that one of your connections is absent of mutual exchange – meaning they’re always taking without reciprocating – now is a good time to shift your time and attention elsewhere. Your mood and productivity will be better for it.


Building Exceptional Leaders