Why You Should Delegate Your Hardest Decisions

4 min read · 7 years ago


Leaders who learn to let go of the ‘big stuff’ stand to make significant gains.

Leaders often have a tough time letting go–especially when it comes to important decisions. Choices that have more limited impact on the business are no-brainers for delegation. But the more integral, strategic, and risky an initiative is, the more challenging it can be for the leadership team to release it.

The leader’s traditional thought process goes something like this: “This is a really big decision that stands to impact the company’s direction and financial future. We couldn’t possibly entrust that to anyone else, so who on the leadership team is going to take ownership of it?”

While this may be your knee-jerk reaction–to assume that the company’s leaders are all-knowing and therefore best-suited to making the tough calls–we’ve found at Pluralsight that empowering others as decision makers can result in creating the type of culture that can move a business forward more quickly. Here are three reasons why you should get comfortable with delegating things you think you can’t.

Delegation fosters trust and empowerment.

Reluctance to give ownership of the tough stuff to your teams indicates a lack of trust toward the people you hired. If you’ve brought in the right players, you can learn to really trust them to make important decisions for you. By doing so, you empower them in their roles to go beyond what you probably would have ever done yourself. When people feel trusted, they can innovate and progress in their own thinking as they move forward toward a decision, which pulls the company forward as well.

You’ll also find that when you let others tackle difficult decisions, they take on a lot more responsibility than you might expect. We saw this firsthand at Pluralsight when we delegated the choice of a new office space an hour south of our headquarters to the team of developers who would be working in that space. We made sure that everyone on the team understood the company’s goals and budget constraints for the new office, and then empowered them to scout and choose a location. We let them assess which space would be the best fit for the future growth of their own group, since they were the ones who would need to drive to that office and work in it every day.

When the developers shared their initial recommendations with the leadership team, we found that instead of coming in over budget, which we might have expected, they were actually more financially conservative than we would have been. They were more worried than they needed to be about committing the company to a long-term expense that wasn’t reasonable, so we had to encourage them to think bigger and more long term. The development team reevaluated and came back to us with another suggestion, and we agreed they were right. By trusting them to make the decision and use good judgment, they were forced to think like any leader would have to think, and they proved to be overly responsible–not careless–with the corporate dime. In the end, they got everything they wanted in an office space, and we still came in under budget.

Delegation empowers true autonomy.

The best leaders learn to give other leaders full autonomy, and this must include decision making. At Pluralsight, we’ve found that when you empower people with enough autonomy to make good decisions, they have even more internal motivation to do what’s best for the company. After the successful experience of the team-centered office-space decision at our headquarters in Utah, we repeated the experiment with our remote team in Chicago and saw similarly positive results.

But we didn’t stop there; the leadership team continued to seek ways to delegate major decisions to the teams. These included setting up autonomous content divisions within our company, in order to delegate all content-related decisions and strategy in a particular topic area to those groups. Also, with our last few acquisitions, we set up a management structure that gives each of the acquired groups autonomy over daily operations and decision making. We meet quarterly to agree on vision, strategy, and objectives, and then we delegate all of the decision making to the groups between those meetings.

Our leadership team has found that when we push back against our first instincts to take care of important business ourselves and instead empower teams to make their own decisions, we’re always amazed by the quality of the outcomes. We continually end up with even better decisions than our leadership team would have made had we attempted to go it alone.

Delegation creates a no-fear culture.

Fear is an enemy of innovation. Fear-based cultures may temporarily make people work harder to avoid negative consequences, but in the long run, they make them less likely to take the type of risks that are necessary for new ideas and progress to flourish.

You can counteract fear in the workplace by–you guessed it–empowering others to make crucial decisions. When people feel supported to experiment and make mistakes on their way to discovering the right choice for the company, the resulting culture becomes one of truth-seeking rather than punishment-avoiding. This is the mindset that’s needed to lead to the innovation and improvements that can become the next big breakthrough for your company. At Pluralsight, we continuously seek ways to do this, which include:

  • Empowering our sales team to do away with sales commissions in favor of a healthier alternative.
  • Empowering our finance team to pick our new accounting system, since they have to use it every day and know the needs better than anyone else.
  • Empowering our data team to choose our data warehousing system and data visualization tools that they use across the company.
  • Empowering our engineering team to undergo the major effort of choosing our new database management system, which we’re moving to right now.

While it’s never easy to release important decisions (which as CEO I’ve experienced firsthand in hiring a leadership team), doing so can serve as a litmus test for your level of trust of other people’s judgment, and their ability to analyze data and seek the truth to decide what’s going to work best for the company. The more you as a leader are willing to delegate hard decisions to those you lead, the closer you’ll be to building a culture that embraces true autonomy and innovation at all levels.

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