You’re Delegating. It’s Not Working. Here’s Why.


 Despite hiring bright minds and able hands, managers often find themselves overburdened and overloaded with tasks. Best practices tell individuals to focus on the highest priorities and delegate tasks to others, especially if it offers the opportunity for growth and development of your team. While this idea is great in theory, many people run into trouble. Delegation is a good idea but often falls flat in practice.

Consider Ali. His 1,000 person company has been at the forefront of innovation — awarding it a nearly $1 billion valuation in an acquisition. Yet he is the hardest working person in his firm, lacks bench strength on his executive team, and routinely disappoints his wife by missing family time.

During a coaching session, Ali and I discussed how he could lighten his load and grow the capacity of his direct reports. An obvious initial idea was to delegate more. However, Ali said, “Delegation never works. I end up redoing work or undoing damage whenever I hand off a major task.”

We unearthed that Ali was using a one-size-fits-all approach to delegation — a strategy doomed to defeat. He identified an item to delegate and then relied on his direct reports to figure out how to execute it or to speak up with questions if they needed to. Unfortunately, not every item or even every employee was suited to this process, and problems were revealed only at the deadline. This left Ali scurrying to pick up the pieces at the last minute.

We crafted a more nuanced strategy yielding greater productivity and less frustration all around. At the heart of this plan is to take time before handing off the task to understand the challenges that could occur once the work leaves our hands and address them preemptively. Here are four common reasons why delegation fails and what to do about them.

Lack of Critical Thinking

Ali often heard a piece of feedback common for executives I coach: “He is brilliant. He can drill down and see things in a way in 15 minutes that no one else had thought of in a month of preparation.” While many of us want to be considered smart, focusing on how others see you can be problematic when overplayed. If you jump in too early and too often with insights, your peers and direct reports will never have an opportunity to develop their own expertise. Confidence also takes a beating when people enter a meeting knowing they will leave feeling less than their manager. And while your insights may be helpful, they’re often offered only after a team has invested weeks of work preparing a presentation. It’s also dangerous to have only one person doing most of the critical thinking in an organization; you could be leaving your company vulnerable to blind spots.

To elevate your team’s capacity to think for themselves, embed the practice of coaching early in the process. Instead of providing answers, ask questions. The quality of their insights will be directly proportional to the quality of your questions. For instance, by asking, “How would our chief competitor respond to this strategy?” one of Ali’s direct reports immediately detected a deficiency in his approach, rather than needing Ali to identify it for him. Open-ended questions allow others to broaden their lens and consider new angles, rather than merely data-gathering queries. Instead of having to supply the solution, you activate others’ critical thinking skills.

Lack of Initiative

Ali was surprised to find that his employees lacked the initiative to make bold moves or even follow up on smaller ones, leaving him nagging and tracking. They would agree to action items that they left incomplete or fail to communicate why they would miss a deadline. Ali also seemed to initiate much of the follow-up discussion and provide areas people might do more homework in. This made him resentful, annoyed that a “delegated” task still stole his precious time, and it left others feeling micromanaged.

If your attempts at delegation are failing because you think others lack initiative or follow-through, address it tactically and strategically. Assign someone to jot down notes, action items, dates, and ownership before the end of each meeting, and start the next meeting following up on promises made. While this might sound basic, nearly half of the executive teams I work with lack of appropriate hygiene in follow-through. More strategically, consider crafting a “placemat”— a one-page document (about the size of a placemat) that lists top priorities. A placemat signals what you plan to reward and provides another way to increase employee motivation. By scrubbing sloppy execution and signaling what truly matters, you can shape up accountability and motivation.

Lack of Quality

Ali had given up asking his team to prepare slides for board meetings. By the time they would deliver the final deck, he was short on time — and had a long list of issues with the final product. Frustrated, Ali would often wipe the deck clean and sacrifice his sleep to make up for a lost time. His team would chalk up another failure with crushed morale.

Instead, unleash your team’s ability to contribute quality. First, provide them with a list of common mistakes and what you would like instead. For example, instead of wordsmithing the title of a slide so it’s shorter, direct your team to deliver slide titles that don’t overflow to a second line. You can even delegate drafting this list to your direct reports based on what they already know about your preferences. Second, instead of fixing the fault, point it out, and request a repair. Annotate a document with comments, instead of redlining it with direct edits. This will take more time initially but save you time in the long run as your team learns what you’re looking for. This may also require earlier deadlines, so your direct reports aren’t submitting final products at the last minute — and that’s ok. By showing them where they can improve, you’ll find that you’ll have better quality presentations and more time in the future.

Lack of Speed

Ali couldn’t understand why people took so much more time to perform tasks than he did. Almost every CEO I have worked with marches to the beat of “CEO time” — a time warp where they either think they can (or they do) complete tasks faster than others. This may be the case because the CEO is more experienced, is clear about what she wants upfront, doesn’t have to spend time divining or iterating to tailor the task, and hasn’t taken into account the extra time spent by employees because they want to look professional in front of the boss.

The next time you have what you consider a “quick” task, ask your team member how long they think it will take. If there is a discrepancy, ask about their process and the reason for the estimate. If necessary, you can help shave off time but removing unnecessary frills or details. For example, they may not need to create a beautiful slide deck but simply write up two paragraphs. On the other hand, you will start to become better educated about what and how long it takes to complete a delegated task and adjust your expectations accordingly.

Managers often experience the push and pull of delegation. We push out the work, only to pull it back again when it fails to meet expectations. By diving deeper into the point of failure, we can better address the underlying causes of delegation failure and encourage our team to be more motivated and productive.