March 31, 2021

Delegating as a Leader: Tips from a Professional Development Expert

Leadership expert Josh Upton gives his advice on how to delegate.

Stepping into a leadership role often means taking on more work, responsibility, and projects. You have to figure out how to balance supporting your team, overseeing projects, and communicating effectively—all while continuing to complete your own work. In order to ‘do it all’ and make room to focus on priorities, delegating tasks is crucial.

At Double, we’ve worked with both first-time executives and seasoned leaders to help them take work off their plates. One thing we’ve noticed is that regardless of how long a person has been in a leadership position, chances are they haven’t been trained in the skill of delegation.

Josh Upton is a Development Partner who works with business owners and leaders in the digital and creative worlds to develop their careers. We asked Josh for advice on how leaders can frame the concept of delegation, integrate it into their daily work routines, and continue to support the teams and individuals they manage.

How would you describe your work and the clients you help?

I’m a Development Partner—a producer, coach, talent manager, facilitator and/or consultant, depending on who I’m working with. I bring my experience in digital production, organizational development consulting, coaching, and music to everything I do. I work with independent creatives, founders, and leaders of startups and larger creative or tech companies.

What does a typical day look like?

My days tend to vary and could consist of 1:1 coaching sessions, tactical meetings with talent partners and teams, creative strategy sessions, team facilitation, or ideation sessions. I thrive on the variety and do whatever I can to continue to level up how I work and keep things organized.

Is delegation a topic leaders often ask for help with?

Absolutely. Relinquishing control is a topic that many of us encounter in our lives both personally and professionally. Commonly, when someone reaches a new level in their career, it can mean taking on more management, and therefore delegation—more people to manage, more work that they’re accountable for, etc.

At this point, particularly with relatively new managers, the shift from doing to enabling the work can be tough. Managers have concerns around work quality suffering, how long it will take for work to get done, and the impact that their team’s work product could have on their own reputation. It’s natural to want to retain control over these kinds of things, but it becomes impossible to meet your expectations as a leader once your direct reports and accountabilities pile up as you progress in your career. What got you here, really won’t get you there.

Is delegation different based on where someone’s at in their career?

The principles around delegation tend to be similar regardless of the level. Frequently, even people who are very far along in their careers have unfortunately never been trained as managers or in delegation specifically.

However, it is common, particularly in the early stages of someone’s career and for first time managers, to feel some extra hesitancy around delegation since so much of their success to that point is based on their ability to do the work as an individual contributor as opposed to delegating or enabling the work to get done through others. This can feel like a loss of control or even in some cases a “loss of identity” (I’ve actually heard people say this), which totally makes sense as it’s a new muscle that people are developing.

When delegating at any level, though, clarifying roles and accountabilities, holding clear kickoffs that address the division of labor at the start of projects, and checking in on how things are being delegated explicitly are practices that anyone can do.

Why do you think leaders have problems with delegation?

One challenge leaders face around delegation is the relatively new expectations many employees have around autonomy and not being told what to do. This is in contrast to more traditional expectations around management—framing a manager as a task master who tells you both what and how to do a task. Many employees are more interested in having flexibility in how they bring their work to life, making for more challenging conversations for managers at all levels.

Additionally, many people just aren’t taught how to delegate and are frequently thrown into management roles, not because they necessarily want to or even know what it entails, but because of traditional models of career growth at organizations. Most people aren’t born knowing how to effectively delegate.

Finally, a lot of leaders are overloaded with more work than they can handle, with endless communication channels to manage (email, Slack, etc.), making it challenging to employ the tact, intention, and care that delegation can require.

Do you recommend any tools, tech, or processes for effective delegation and work management?

Any tool, technological or analog, that makes roles and accountabilities explicit will can help— RACI docs, a simple Google doc, high falutin software, Post-it notes—the format is less important than the act of being explicit about roles, responsibilities, and the things that will be delegated throughout the course of a project.

Having explicit conversations around workload and delegation in 1:1s with your direct reports is key as well. I recommend including a discussion around communication style and how the leader and the direct report have handled delegation in the past. Sometimes, just asking how clear someone is on what’s on their plate and what their expectations are can work wonders, as simple as that sounds.

Finally, enacting weekly tactical meetings with teams can offer a rhythmic chance to reiterate expectations around tasks in a team setting and make sure that everyone is aligned.

Do you have advice for someone in a leadership position who’s struggling to do it all?

  • Make delegation an explicit topic in your 1:1s or team meetings as a skill that everyone can work on. Let people feel safe talking about work in progress.

  • Have an explicit conversation with team members around the clarity in their role. Use a project to run through so you can apply a delegation lens to it—for example, “We’re launching this website, I’ll be the one to set the strategy and then you’ll take that and convert it into a project roadmap.”

  • Move beyond the what and always include the why. How does this task being delegated play into the purpose, strategy, or intention of the bigger picture or goal of the project?

  • Always save time for questions. This is a two way conversation and you want the delegatee to be clear on what’s being delegated to them and what good and complete looks like.

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