Playing the Hand You’re Dealt

This spring, I lost a few dollars (happily) at a local nonprofit’s casino night. It was for a good cause, and I always leave these events grateful that I don’t gamble regularly—and that I can feel great about losing, which is hard for my Type A overachiever self.

The winnings could be cashed in for raffle tickets for a bunch of stuff I didn’t want, so the only objective was to give money away. (Unlike the unintentional giving away I’ve been known for in other contexts.)

I spent most of the night at the blackjack table.

Now, let me confess: I’m a bridge player. I don’t play for money—just for competitive fun. The American Contract Bridge League awards points, which are worth absolutely nothing but do get you into rooms with other people who think points are something.

Bridge is a game where you’re dealt 13 cards and must partner up to make the best of what you’ve got. I don’t mind that (though it can be demoralizing to pick up bad hands all night).

Blackjack? You can ask for more cards!

Poker? You can give some cards away in hopes of getting better ones!

Once again, I could not escape reflections on – and connections – to leadership while playing cards to support a nonprofit. That’s the hand I was dealt in this life (and the hand I love to play.) 🃏

Especially in the current moment, many nonprofit leaders feel like they are gambling – whether money is involved or not. Should you accept the hand you were dealt? Take a chance and risk overstepping? Or give something up in hopes of a better outcome?

In leadership, there are times when we:

• make the best of the hand we were dealt (like in bridge),

• carefully add to our holding, not risking overstepping or overstaying our welcome (like blackjack), or

• give something up to create space for what serves you better (like poker).

So, how do you know which game you’re playing—and what the best strategy is?

When It’s Bridge: Make the Best of What You’ve Got

There are lots of bridge moments in nonprofit leadership – times you just need to manage the things you cannot change in as smart a way as possible.

• A major funder changes their priorities (and, sorry, you’re not one of them)

• The board you inherited seemed so on top of everything during the interview process but not so much now that you are in the role.

• A natural disaster hits your area – threatening the wellbeing of your communities, your team, your board – everyone.

A classic “bridge” moments is when a leader joins a new organization. When I coach new leaders, I tell them that year one is bridge.

What you find on your first day is just different than what you were told to expect. You don’t control the cards, but you can play them well – keep things running, build trust, and prepare for change. And sometimes cards that looked worthless when you picked them up turn out to be winners later in the hand.

Even bad cards can be played well. You can’t alter the current state of affairs, but you can go about managing strategically, proving you have solid leadership chops, and set yourself up for bigger wins in the future.

When it’s Blackjack

Some moments are more like blackjack – you have some say in the outcome – some influence – but you need to weigh your next move strategically.

• You’re advocating for policy changes as part of a coalition (but not in the lead role)

• You’re wooing a new donor who supports similar organizations – you want to push but not too fast or seem presumptuous

A classic “blackjack” moment is managing an enthusiastic new board member – someone passionate about your mission, full of new exciting ideas, but still learning the ropes. You need to balance supporting and guiding – not being a wet blanket but also making sure you aren’t encouraging them to the point of overtaxing your team or getting out ahead of your board.

In this situation – and ones like it – your job is to decide: Do you stand, hit, double down, or split? The key is to stay in the game without overplaying your hand.

When it’s Poker

Other times, the ideal move is to give one, two, or even three things up in hopes of making room for bigger opportunities and deeper impact.

• You rebrand – change your visual identity and/or name because they no longer reflect who you really are.

• You finally say no to a funder who wants a lot more than their grant really pays for.

A classic “poker” moment is when you decide to sunset a legacy program that doesn’t pay for itself or reflect your new strategy – but everyone loves it all the same. There’s no guarantee that stronger programs will step in right away—but they never will as long as the legacy one stays in place.

Getting clear about assets that you need to retain versus some you could sacrifice can help you have a winning round.

So … Which Game are You Playing?

When you are facing a challenge, ask yourself:

♣️ Do I have control over what is happening?

• Yes? It’s either blackjack or poker. Keep reading.

• No? It’s bridge. Figure out the smartest move you can make that is within the constraints you have – and don’t expend effort trying to change what you can’t.

  
  

♠️ Do you have influence, but not full control?

Yes? You’re playing blackjack. Evaluate the consequences of:

• standing (staying put),

• hitting (making a calculated move), or

• doubling down (going all in).

  
  

♦️ Do you need to give something to move forward?

Yes? You’re playing poker.

Decide what you can jettison – legacy programs, draining partnerships, fruitless meetings – to free up capacity to be focus and ready when opportunity comes knocking.

Remember: a lousy hand in one game might be a winning one in another. Whatever the game, you always hold high cards—your mission, vision, and purpose. And hopefully, your board, team, and donors increase the value of your hand.

Good leaders are opportunity focused. Even amid uncertainty and pressure, they look for the best way to play the hand they are holding. You won’t get to everything. Some lines of play will be obscured, some blocked, and some will open unexpectedly.

Whether you’re holding aces or bluffing through a rough round, it helps to have a good partner at the table. Email me at gary@garybagley.com or DM me on LinkedIn.