How to know when to say yes

“In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.” – Theodore Roosevelt

How to Know When to Say Yes

By Andrea Novakowski

Jennifer, the owner of a supplier to the biopharma industry, was approached by a business connection with a new idea to invest in. Because she was a great networker and business person with lots of connections, these opportunities often crossed Jennifer’s desk. “There are so many ventures to participate in,” she told me, during our coaching session. “How do I choose?”

Last month, we talked about how to say no when situations arise that don’t feel right to you. The next big question is, how do you decide when to say yes?

Jennifer knew herself well, and she was aware how easily she could be distracted from her commitments by the next new shiny thing. The crux of our discussion was how she might judge which opportunities to pursue, and which to let go.

We talked about the best “yes” decisions Jennifer had made in the past. Then we looked at how she’d made those decisions. Based on that information, Jennifer created a set of three questions to ask herself whenever a choice came up. Here they are:

What’s the growth opportunity for me or my business? One of Jennifer’s core values is learning. If a project or idea gives her a chance to expand her knowledge about her business or herself, it may make sense for her to go for it. When it gives her the opportunity to do something she’s never done before or travel outside of her comfort zone, it allows her to grow and stretch.

Does it fit with my goals? As Jennifer weighed each opportunity, she reviewed her long-term and short-term goals to see if this action aligned with what she wanted to accomplish. For instance, one of her goals was to have a diverse portfolio of businesses. So she needed to examine each investment opportunity to ensure she wasn’t putting all her eggs in one basket.

What’s the cost of this investment? You might think money is the only cost to consider, but time and effort are costs, too. Checking in with your head, heart, and gut is part of assessing these costs. A clenched gut could mean the cost is too high, while an opening of your heart might mean you’re willing to invest. (Hint: If the cost is more than you want to pay, see if you can find some ways to limit your risk, such as investing in a more modest way. It’s not always all or nothing.)

After devising this simple 3-question process to guide her decision making, Jennifer felt more confident about her ability to choose what new projects to take on. She knew if she asked herself these three questions and the answer was yes, she’d go for it. If it was no, she’d take a deep breath and let go.


It’s your turn: What guides your knowledge that an opportunity is a good fit for you? What three questions can you ask yourself when something new comes up?

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