Have you ever delegated a task to someone, only to discover that they didn’t give it the same level of passion, determination, and expertise that you would have invested in it? 

Feeling disappointed by others’ execution on your high expectations may leave you less likely to delegate crucial tasks in the future. Media, podcasts, LinkedIn posts, workshops, seminars, and books all tell you how important delegating is, but if you’ve been burned before, delegation can feel daunting and risky. 

How do you turn things around when you feel this way? At its best, delegation should feel liberating, not anxiety-provoking. One way to feel better is to realize that delegation of tasks should never go to an unskilled subordinate. Rather, you always want to delegate crucial tasks to proficient team members who will even outperform you. 

But delegation doesn’t come naturally to many startup execs. Delegating is actually a skill, one that leaders should constantly be mindful of and should work to hone. While setting the right conditions in the right environment is crucial for delegation, so is having the right mindset.

Find TL;DR section at the end of this article

The question lingers for all leaders of scaling teams: Are you good at delegating?

Delegating is a crucial skill for leaders of scaling teams, but it is not enough by itself. 

However, even if you are good at delegating, you may still face challenges in scaling your team if you do not have the right team members, enough resources, or a clear vision.

Delegating to the wrong people, or to people who are not capable, motivated, or aligned with your goals, can lead to poor results, wasted time, and frustration. 

That’s why delegating effectively requires not only assigning tasks and responsibilities, but also selecting, developing, and empowering the right team members who can help you achieve your vision.

Delegation is the path for growth

Instead of giving into fears about delegating and burdening themselves with every task, leaders should learn to acknowledge that productivity is best fostered through team effort and accountability.

As a starting point, executives often discover that delegating administrative tasks enables them to concentrate more effectively on activities related to business growth and development. Admin responsibilities, such as email and calendar management or travel planning don’t require the skills of a VP or a CEO, freeing you up to focus on higher level items on your to-do list.

Delegation is more than just giving a task to a team member and expecting them to complete it without further guidance, examples, or deadlines. Delegation also requires trust in the team’s abilities, feedback on their performance, and a safe space where they can share their opinions and ask questions.

Jane, a CRO at a Series C startup, is not good at delegating

“Each delegated task must be both time-consuming and well-defined. If you’re running around like a chicken with its head cut off and assign your VA to do that for you, it doesn’t improve the order of the universe.”

― Timothy Ferriss, The 4-Hour Workweek

Jane is a CRO from a Series C company based in New York. She’s been working hard with her VP of Product and VP of Marketing on developing pricing strategies to enhance customer acquisition and reduce churn. At the same time, she’s had to educate herself on the industry’s laws and regulations, which have changed considerably in the past few months. While all of this is happening, the marketing team wants to make sure that their communication strategy has correct information before rolling out their campaign; for this, they need to meet with Jane on a weekly basis, supplemented with daily async communication. 

These core responsibilities generate a massive amount of administrative and tactical tasks that require different levels of competence and skill in order to be performed at the highest level of quality while staying on a timeline. The work can’t be done poorly or delivered late. 

The CRO knows exactly what she wants, so she figures it’ll be easier to just do it herself. She’ll probably waste more time explaining and reviewing it, she thinks. Jane also doesn’t trust her team to be able to complete the task with her full list of requirements by the requested deadline. 

Unfortunately, the DIY approach also generates countless meetings and calls that require active listening and the CRO’s full attention. This means no multitasking.

Startups often require leaders to wear multiple hats, but attempting to handle every task personally can lead to an overwhelming workload. This can result in burnout and decreased productivity, ultimately compromising the person’s health and the company’s growth. There are no winners when burning out. 

Even though Jane is a very skilled and competent CRO, her job is not about doing admin and tactical tasks. It’s about building strategies, leading her team, and working hand-in-hand with other departments within the company. This lack of focus on core responsibilities may hinder company growth since Jane won’t be able to set her pricing strategy in motion and her plan to reduce churn might never see daylight in time for the next billing period. 

While Jane is feeling overwhelmed working 16-hour days, impacting her work-life integration, her team is feeling underutilized and undervalued because they are not being given challenges or trusted with high-impact tasks. She is risking employee turnover. 

Days go by and Jane is putting in more hours, more effort and she is growing more tired and less focused. The deadline is approaching fast and her goals are not being met. 

Her inbox and Slack messages are overflowing with questions from team members who will not make a decision until they hear from her, but Jane is unable to answer. There aren’t enough hours in a day. By refusing to delegate, she is becoming a bottleneck in the decision-making process.

To make matters worse, her two kids woke up with a fever. They need to see a doctor right away but if she doesn’t show up at the office, no work will be done. She doesn’t have that luxury, but also, she doesn’t have a choice.

It’s finally come to the point where Jane can’t choose to delegate or not: if she doesn’t get the team involved, chaos will ruin all of her hard work strategizing for the next quarter. Now her team has a tight deadline and very few instructions from the CRO, who is OOO and unable to take calls or answer messages. 

Jane is desperately in need of delegation help. It has to be done quickly and with the least number of mistakes possible. 

Delegation is a skill that can be learned

No startup exec wants to find themselves in a situation like the one Jane was in, but you may know yourself how common this scenario is. You may even be familiar with how devastating it can be to a startup leader’s health and well-being, team morale, and company performance. 

But it doesn’t have to be that way. 

Delegation tends to be tough for many startup leaders, who are skilled in multiple areas, want to move fast, and need to perform and generate impressive outcomes. Though delegation may not come naturally, it is a skill that can be learned. And like most skills, delegating gets easier the more you practice it. 

If you’re unsure about whether you’re effective at delegating, or if you want to know the areas of skill-building within delegation, read on for our top tips.  

5 signs that you are a great delegator

“The only reason you struggle to delegate is because you are not clear of how to achieve the results.”

― Chinmai Swamy

1. You have a defined strategy for delegating

Alex Lieberman, cofounder of Morning Brew, realized he was bad at delegating after a prolonged trip (1.5 months) that kept him away from the office. Lieberman noticed that progress slowed when he wasn’t around.

Besides work not getting done at normal speed, he also realized that his peers and team members had unused capacity due to his lack of delegation skills. It wasn’t that his team didn’t want to help or move faster; they didn’t have the information to do so.

Lieberman first needed to understand why he was delegating poorly. The second thing he needed was to learn how to delegate well. This is where he learned to use the Eisenhower matrix. 

The Eisenhower Matrix classifies tasks into four quadrants based on their urgency and importance: urgent and important, not urgent but important, urgent but not important, and neither urgent nor important.

Eisenhower matrix, source: Google.

You should have few items in the important and urgent axis. Lieberman advises to focus on completing one significant task every day. Viva’s own Fineas Tatar recommends focusing on 3 key priorities a week. Anything else might be overpromising and underdelivering. 

Read more on delegating and the Einsenhower matrix. 

2. You trust your team on different levels

Great delegators understand that trust is a multifaceted concept. The “Six Levels of Delegation” offers a framework for recognizing and utilizing different levels of trust in the delegation process. 

These levels range from “Do exactly what I say” to “Decide and take full responsibility.”

To be an effective delegator, you need to assess each task and match it with the appropriate level of trust based on your team members’ skills and experience. 

Routine or straightforward tasks can be delegated at lower trust levels, while more complex or strategic responsibilities are entrusted to team members with higher levels of skill and expertise.

This tailored approach not only empowers team members, but also fosters their professional growth and skill development. By acknowledging and adapting trust levels, great delegators maximize their team’s potential and cultivate a culture of accountability and ownership.

As Alex Lieberman says, “Most of your time as a manager is moving people from level 1 to level 6 of trust,” meaning that instead of doing the tasks themselves, leaders should be focusing on upskilling abilities of their team members so that they’re able to delegate more tasks and authority.

“Trust is powerful. It is also fast. It can be lost quickly. Trust is also reciprocal. If you give trust, it will be given back to you. Delegation is a result of this trust.”

― Steven R. Covey

3. You give clear instructions with examples and make room for questions

When you communicate your expectations clearly, you set your team members up for success. They have a precise understanding of the task at hand and the desired outcome, which makes it easier for them to deliver the results you are looking for. This not only saves time and prevents frustration, but also builds trust between you and your team. 

Team members appreciate clarity and are more likely to feel confident in their ability to complete the task as requested. 

Processes are essential for organizations that perform repetitive tasks, as they ensure that the tasks are done in a consistent, efficient, and quality manner. 

By creating a clear and standard framework for task execution, processes reduce the chances of errors and variations, while also enabling scalability and accountability. 

Moreover, processes make it easier to train and onboard new employees, as they provide them with clear guidelines and expectations. Processes also help in risk mitigation, by identifying and addressing potential issues.

There are still more benefits. Orgs with processes do a better job of gathering useful data for analysis, which helps them improve and adapt to the changing business environment.

Besides processes, leaders should create a culture where their team members can ask questions, challenge assumptions, and express dissent. This way, they can foster more collaboration, innovation, and learning.

On the other hand, leaders who use coercive language, as described in Leadership is Language, stifle the autonomy and creativity of their team members. They make it hard for them to make decisions or speak their minds while performing certain tasks and duties.

This is especially important because team members’ perspectives and opinions may foster growth and avoid problems. 

“Another way of building trust is to authentically delegate. Don’t assign someone work and then constantly monitor their progress and ignore their ideas.”

― Scott Sonenshein, Joy at Work: Organizing Your Professional Life

4. You have plans to upskill team members so you can delegate more authority to them

By helping your team members develop their skills, you’re preparing them to take on more significant responsibilities. This not only lightens your workload, but also creates a more versatile and self-reliant team. 

It’s a win-win scenario where team members benefit from professional growth, and you benefit from having more capable individuals to whom you can delegate. This commitment to upskilling fosters a culture of continuous improvement and demonstrates your dedication to both your team’s and the organization’s success.

How to plan for upskilling your team so you can delegate more

The 1st step to upskillng is doing skills assessments to identlify improvement areas in your team.

Once you know your team’s needs and wants, find training programs, workshops, certifications, e-learning platforms that align with the desired outcome.

Another great upskilling initiative are mentorship programs where senior team memebers guide and share their expertise with those who are looking to develop specific skills.

Some companies are using gamification strategies to build e-learning processes for their employees by giving rewards, rankings, or levels to motivate their teams to learn new skills, earn degrees, or collaborate on specific projects. 

Fostering a culture of continuous learning is crucial; this can be done by making learning resources readily available, encouraging experimentation, and recognizing and rewarding proactive learners. Leveraging technology for e-learning and providing accessible knowledge-sharing platforms can also help in upskilling efforts.

Executives should lead by example and actively engage in their own learning and development, creating a culture of growth within the organization. 

Monitoring progress, budgeting for upskilling initiatives, and celebrating achievements are also important elements of a successful upskilling strategy. 

By systematically and consistently investing in their team’s development, startup executives not only empower their employees but also enhance the startup’s overall competitiveness and adaptability in the dynamic business landscape.

5. Your team is able to work without you

“Focus on what you are good at; delegate all else. Jobs doesn’t direct animated movies or woo Wall Street. He concentrates on what he’s good at.”

― Leander Kahney, Inside Steve’s Brain

Did you go on vacation and nothing broke while you were OOO? Congrats! It’s probably because you’re doing a great job delegating.

In the book Language is Leadership, author David L. Marquet shares the story of the ship El Faro, the worst US maritime disaster in three decades. 

He discusses how the tragedy could have been prevented if there had been more delegation on the ship. The captain, Michael Davidson, used an outdated Industrial Age playbook that divided the workforce into “blueworkers” and “redworkers”. According to Marquet, blueworkers are those who think and decide, while redworkers are those who do and obey.

The captain was the only blueworker on the ship, while the rest of the crew were redworkers who had to follow his orders without question. This created a culture of compliance and conformity, rather than collaboration and creativity. The crew did not feel empowered or encouraged to share their opinions, challenge assumptions, or question the decisions of the captain. As a result, the ship sailed into a deadly hurricane that could have been avoided if there had been more delegation and communication on board. 

Marquet contrasts this with his own experience as a submarine commander, where he implemented a new leadership model that he calls “leader-leader”. In this model, everyone is a leader and a follower, depending on the situation. 

In such a team, everyone is a blueworker who can think and decide, as well as a redworker who can do and obey. Marquet empowered his crew to take ownership of their roles, to speak up when they saw a problem, and to make decisions based on their expertise. 

This approach created a culture of trust and innovation, where the team was engaged and motivated. As a result, his submarine became one of the best performing in the US Navy, achieving remarkable results in safety, quality, and efficiency.

The story of El Faro and the story of the submarine illustrate the importance and the benefits of delegating and how it can drive a team toward failure or success. 

In the submarine example, the team continued to be the best performing in the US Navy even after Marquet had already left and his leadership position had been replaced. 

Summary: TL;DR

These are the 5 signs to know if you are a good delegator:

1. Define a delegation strategy:

•   use frameworks like the eisenhower matrix to categorize tasks based on urgency and importance.
•   focus on completing significant tasks daily or prioritize key priorities weekly.

2. Define levels of trust per team member:

• recognize and utilize different levels of trust in delegation, ranging from specific instructions to full decision-making authority.
• tailor trust levels based on team members’ skills and experience, empowering them and fostering professional growth.

3. Make sure that your communication is clear:

• provide clear instructions with examples to set precise expectations for team members.
• create a culture where questions are encouraged, fostering collaboration, innovation, and learning.

4. Make a commitment to upskill your team’s talent:

• invest in skills assessments to identify improvement areas.
• implement training programs, workshops, mentorship, and gamification strategies to upskill team members.
• foster a culture of continuous learning by making resources readily available and encouraging experimentation.

5. Foster team independence:

• measure delegation success by the team’s ability to function independently.
• contrast the consequences of a lack of delegation on the ship el faro with the success of a submarine crew under the “leader-leader” model, highlighting the importance of delegation in driving team success.

Interested in more leadership tips? Read our article about finding purpose in your leadership.