For IT leaders, opportunity is so plentiful that it can become impossible to even focus on the boundless chances we have to leverage new products, implement a new management philosophy, or hire a talented individual who just came onto the market. Here are several tips for recognizing and exploiting the right opportunities.

Perform a “three-way test”

Just because a favored vendor appears with something billed as an opportunity doesn’t mean that it’s necessarily helpful to you or your company. For an opportunity to be worth exploring, it needs to pass a three-way test of sorts:

  1. Is the opportunity valuable to you?
  2. Is the opportunity valuable to your IT organization or group?
  3. Is the opportunity ultimately valuable in the broader context of your company?

Note that the vendor or entity offering the opportunity doesn’t figure into this initial evaluation, and in the IT space the opportunities you’re presented with will often be those that make the most sense for the vendor, and not for you or your company.

The best opportunities provide some immediate benefit to you directly, providing a solution to a problem directly in your purview. While seemingly selfish, an opportunity with personal benefit is one that you’re likely well positioned to vet. If you’re constantly playing the part of disinterested evaluator, you’re less likely to take the initiative to fully realize what might be a time-sensitive situation.

With a personal interest, consider how the opportunity will impact your department, as well as the larger organization. Some opportunities will satisfy all three constituencies, while others may be at odds in some or all dimensions. For example, outsourcing your department may be the right move for the broader organization, but obviously less compelling for your department and potentially your individual success. With significant conflicts, consider passing the opportunity along to someone else if it provides legitimate benefit, as they may be better positioned to exploit it.

Engage a trusted party

If an opportunity comes your way that can’t be quickly evaluated in the context of the above test, consider engaging a trusted third party — this could be a colleague, a subordinate, or even a trusted vendor who can provide feedback that’s appropriate to your organization. Be aware that this third party will apply their own three-way test, and thus their judgment will be influenced by their perspective. Also avoid subjecting this person to “opportunity fatigue,” which may result from passing them anything that comes across your desk.

Measure the risk

With an understanding of the benefits to yourself, your immediate organization, and the larger company, and potentially the help of a third party, it’s worth evaluating the risk of pursuing an opportunity. Everyone has a limited amount of time and attention span, and thus you must pursue opportunities wisely.

A critical factor in determining if an opportunity is worth further investigation is to quickly analyze the risk of pursuing vs. ignoring the potential opportunity. Highly experimental software might be personally interesting, a boon to your department, and have the potential to support a new corporate initiative, but it might be more risky than a chance to streamline an uninteresting but high-volume process when the benefits of each are taken into account.

Follow your gut on the timing question

Most true opportunities are time sensitive. That great candidate who just appeared on the job market won’t be there in a month, just as an emerging technology won’t be unique to your company forever. People who are peddling opportunities know this, and may attempt to create false urgency to force you to move forward.

If something feels amiss, don’t let the pressure of a “one-time offer” force you to abandon a sensible investigation into the risks and rewards of pursuing an opportunity. This must be balanced against an overly aggressive desire to avoid risk, a tendency that is easily identified after you miss several legitimate opportunities due to an inability to make a decision.


Taking the time to assess opportunities, vet them with a trusted party, measure the risk, and manage timing can turn a seemingly overwhelming task into one that becomes manageable. The alternative – that is, ignoring all comers — is a recipe for stagnation. Diligence can prove beneficial to you, your department, and your company.