10 Successful Entrepreneurs on Why Delegating Effectively Is Difficult But Necessary
Grow Your Business, Not Your Inbox
The ability to effectively delegate can be one of the most effective tools a good leader can use. Without the ability to delegate one becomes “the bottleneck of their own success." While this is of course true, delegating can be hard and requires a great deal of trust in one’s team. There is also the persistent voice in one’s head that argues that “if you want something done right you need to do it yourself." So how do leaders delegate effectively in a way that allows them to be completely satisfied with the results?
Authority Magazine recently starting an interview series called “5 Things You Need To Delegate Effectively and Be Completely Satisfied With the Results”
We interviewed successful CEOs, founders, and business leaders who shared advice from their experience.
Carla Williams Johnson, Carli Communications
Get clear on what you need. Who (or what) do you need exactly on your team to ensure things run smoothly? What are the strengths this candidate must possess in order to get the job done or is it something where investing in a system might be a better option.
Know your strengths. Decide what are the highest generating activities that only you can do, then prioritize all other activities that are important but can be delegated out. Be sure to include instructions of what you need, the desired outcome and expected timelines.
Learn to let go. Trust yourself that you’ve made the right decision and resist the urge to micro manage.
Be open to doing things differently. The person you delegate to may have their own ways of getting things done that may be different from what you’re accustomed to; be ok with it.
Encourage feedback. Let your team know that they’re doing a great job or if there’s room for improvement. Also allow them to open up to you if they feel stuck and need assistance.
Tom Giberson, Lead Grow Change
Accept that you have no idea what people think about you, and you can’t do a whole lot about it anyway. Some day, you’ll stop letting that thought pattern hold you back. Leaders who worry too much about what others think about themselves — and therefore avoid delegating, difficult conversations and so forth — are self-imprisoned. This is a quite common phenomenon for all of us, not just leaders. We’re wired to get along with the tribe so-to-speak, and people who don’t get along are cast out. Projecting the impact of our behavior on others and their response is an important survival skill. However, as a leader, you’re in a position of power, so do your job! Think about how much time you spend each day making negative judgements about your boss, peers, direct reports. Hopefully, that doesn’t consume much of your time. The same is true of people toward you. They spend little time thinking about you. They’re just as wrapped up in their own heads as you are, worrying what others might be thinking about themselves. “She’s just doing her job,” is what they say to themselves when you do something they don’t like, such as delegate a tough or undesirable responsibility.
Frame your success as your team’s success, not as your involvement with the content of the work. Work the people, not the problems your people are solving.
Trust others to do the right thing until proven otherwise. If you don’t, then you’re hiring and leading incorrectly. If you simply can’t learn to trust others, you belong in an individual contributor role — and there’s nothing wrong with that.
Role model and reinforce leading through vision, anticipating what’s next, and planning, rather than simply executing. This requires that you hold people accountable for and reward “preventing fires” rather than putting out the ones they failed to prevent.
Remember, we're all human. And to be totally honest, I think that it is not possible to be completely happy with the results. We’re all human and are fallible. So, no different than anything else performance-related, results will vary! What’s important is to focus on the process and creating a context and culture of ownership and empowerment.
Agostina Pechi, Goldman Sachs
Well-defined responsibilities. It’s certainly number one. Define and clearly communicate to employees your goals and what you are expecting from them and let them handle it their own way. For example, we set high level objectives on a quarterly basis, and on a weekly basis discuss more specific business objectives. Especially as responsibilities can shift or grow during turbulent times, it is critical to focus on defining these responsibilities and clearly communicating them.
Make sure you have the right person for the job . You need to really know your team’s weaknesses and strengths, and find the right person for the task. For example, each member of my team has a unique background and brings a unique perspective. If we are analyzing a transaction that has a certain feature or is in a certain jurisdiction, or would otherwise involve some particular sort of background, it is important to reflect on each individual, and the combined strengths of the team, to staff most efficiently.
Have an open-door policy . It’s essential to be open to your team member’s suggestions, concerns and feedback. This will ensure important information reaches us and we can make necessary improvements and tackle every problem. For example, I implement a weekly email follow up or in person catch up just to give some cadence to our interactions. So, I don’t wait until they come to me with an issue or progress. That way those checkpoints are well defined and I’m relaxed that I will be posted on the progress in a certain period of time.
Identify clear targets and objectives . Even when responsibilities are well defined and the right person is chosen, it can be hard for the individual to envision what you think is an optimum outcome. For example, onboarding 10 new clients is good for me, but for the individual onboarding 3 is good enough. And when we get to the performance review, we realize that each of us were targeting different results. Another example is that, sometimes people tend to think of projects in phases. Providing the overall picture and discussing what is expected will allow for timely results and realignment of goals when needed.
Check regularly with the team and trickle-down information. With ever-changing market and economic conditions, we find that business priorities change as well. We need to implement a culture of communication and frequently touch base with the team to share the "big picture" and provide feedback on their progress. In my opinion keeping the team informed builds the culture of transparency and encourages them to do the same within the team. This flow of information results in better outcomes. As an example, this type of communication and swiftly transference of information was critical during the COVID-19 pandemic, as we quickly prioritized or sidelined certain initiatives at the management level.
Michael DePrisco, Project Management Institute (PMI)
Empathize. With work and life becoming more intertwined due to the pandemic, it is important to recognize that some folks may not be coping well with a virtual situation or may be juggling more responsibilities than you realize.
Start with the end in mind. When delegating, aligning on a common goal with your team or team member is one of the first steps that must be taken. Having a vision of how a project should be completed not only provides a blueprint, but also may determine who you ask to step in on certain responsibilities.
Establish your roles and responsibilities. Especially if you are delegating to a team of professionals, it is important to establish clear roles and responsibilities to show the team how it will collectively reach the final goal.
Communicate, communicate and communicate along the way. This is now especially important as we work virtually, but even in a traditional office working environment communication is critical. Helping your team members prioritize deliverables to meet deadlines will save headache later and make the team more efficient.
Reward, recognition and acknowledgement is key. At the end of the day, as you delegate tasks to team members, it is equally important to recognize and reward quality work. In many cases, delegating work can see team members rise to an occasion or go above and beyond a project ask — it is important to acknowledge the effort, skill and talent that goes into successful deliverables.
Anahita Dalmia, Alterea
Plan effectively .There are a number of factors to consider while delegating: the time to onboard someone compared to the time to do it yourself; the skills, availability, and interests of the person you’re delegating to; as well as team dynamics. Delegating is an early investment of time to create a better product than you could have made alone. Yet when badly planned, it typically leads to miscommunication, wasted time, a subpar product, and frustration on all ends. When I asked a teammate to write up a post for recruitment which was a one time task and I had clear specifications for, it took me as much time to edit their draft as it would’ve taken me to write it myself showing that that was bad delegation. But there is no way I could’ve written 15 scripts for the same project, so it was necessary to onboard a dedicated writer.
Delegate to the right people . I remember once we were working on a project and I asked the team, “Who would like to do this? You know, Jasper, you’re pretty good at this…” Even though it was a boring note-taking task, Jasper had laughed and quipped “Ah yes, flattery is the best form of delegation.” While the action was mostly subconscious, if you delegate to the right people then they should be able to do the task better than you would have been able to and draw some level of satisfaction from doing it. Each teammate brings unique strengths that are needed to complete the goal and, in the best teams, it’s almost intuitive who will be doing what task because each person’s role and capabilities are so clear.
Find optimal level and style of collaboration and communication. Each person functions differently and it’s important to understand what resources, information and support they need to do their best work. Some people need one page write-ups of assignments with examples, inspirational references and the criteria for a good deliverable. Other people just need goals. Some people prefer sweetened feedback and time to arrive at the conclusion you reached, with suggestions on how to fix problems. Others want to-the-point feedback and space to figure out appropriate solutions themselves. When I take the same problem to two of my teammates, one of them wants to talk until they find out how to fix it and another always asks if we can come back to this in a few hours so he can think about it. Both are fine, but it’s important to give each such teammate the space to ask for what they need and provide it to them.
Empower them to own the job . We don’t use the word employees, we use the word ‘collaborators’. We make sure everyone is aware of their contributions to the big picture and that the end product is our collective responsibility. Our teammates volunteer for jobs, even though we suggest who we think may be best suited to fulfill it. This makes people take more ownership of what they are directly doing — but we keep them involved in things they’re not directly responsible for as well. While developing our most recent project, Agents of Influence, each game designer pitched a game and was responsible for its execution. But they workshopped different games, gave extensive feedback to others, and incorporated detailed suggestions to make a product that was far from only theirs. They took responsibility for its development and, many times, they held themselves to even higher standards of performance than I would because of their pride in what they were working on.
Trust and respect . One of my teammates once joked that, even when they know they’re doing work for me, I make it feel like a privilege for them to do so. And the heart of that is really trust and respect. I always pick the best people to accomplish a task, so when I ask someone to do something they perceive it as a compliment to their abilities. It’s important to give teammates almost complete control of whatever task they’re doing, even while providing guidance and goals, as they should do it better than you can. Furthermore, to be respectful of people’s time and retain their trust, be completely transparent about what people gain by working with you — compensation, recognition, appreciation, an opportunity to learn something new, and, sometimes, even nothing — with an opportunity to turn down the ask. Unless people trust each other and respect their abilities, delegation is impossible.
Joel Patterson, The Vested Group
Learn your team members’ strengths. You can use several assessment tools to determine your team members’ strengths — my favorite is Gallup StrengthsFinder, but you can use whatever suits your needs and allows you to be consistent. Have your team members take the strengths assessment as part of the onboarding process, and you’ll find value in weaving this knowledge into all kinds of interactions, even beyond delegation.
Learn what each strength brings and needs. This one is key: beyond identifying your team’s strengths, you have to be committed to learning how each power contributes value and what each strength needs to draw energy from. Our organization has found great value in partnering with a business coach who meets with team members individually and in groups to explore the strengths in depth. Armed with this knowledge, you can choose the tasks and projects best suited to particular team members. You’ll be scratching your head at how easy it is to delegate once you can pair the employee with a role seemingly tailor-made for them.
Communicate with transparency. Once you’ve identified who you will delegate something to and why be transparent in your communication. Let your team members know that you see what makes them exceptional, and you want to tap into their strengths with an opportunity to shine. Sharing your specific reasons behind thinking they are the best person for the job not only validates their strengths, but it also shows your authenticity in selecting them to tackle the task.
Debrief. Once you’ve delegated a task or project, make sure you follow up with your team once the job is complete. You’re not checking for completion — ask them if they felt like the right person for the task? Did they feel like they had what they needed, both internally and externally, to be a smashing success? Were they challenged and engaged by what you delegated? Explore their feedback, and you’ll be able to evaluate your delegation skills based on their responses.
Trust yourself and trust your team. Once you’ve made an informed decision to delegate, do so with confidence and then let the group you’ve chosen take the lead. One of the worst things you can do when delegating is to stick around and stay involved — this undermines the team you’ve chosen and doesn’t accomplish opening up time and space for you to do other things. The beauty of being skilled at delegating is you can turn tasks over to people and teams you know will be successful.
It’s time to let go! We have to accept that we can’t do everything yourself, it is critically important. Giving up that control takes perseverance and perspective. We have to remember that letting go allows space for more success not less. Giving your team the responsivity will elicit confidence and dedication to the mission.
Count on your teams’ strengths. Knowing the teammates’ strengths and leaning into them is your goal. Take a look at your team and delegate tasks based on their assets not their workload. Too many times we think because someone isn’t busy, they can do the job. NO!! Full STOP! It’s about skill not availability.
Get them to invest in the outcome. The crucial point in delegating successfully is making sure the person you are delegating to is fully invested. — Just giving a task to a team member without an explanation of why it’s important or why their skill set is best suited, won’t get you the results you need.
Are you set up for success? Describing what your needs are around the task and communicating the deadlines are crucial. If your team could read your mind, please tell the rest of us. Your explanation needs to be specific and include your expectations. The worst that could happen is confusion around what needs to be done and when. Saying, “Beth, could you take care of the marketing content? Is vastly different, then, “Could you look at the marketing plan for XYZ and let me know the five steps that needs to be taken for us to ABC by Friday at noon?” Clear and concise direction with time constraints.
Don’t expect perfection, your team is not you! NO ONE will do anything like you do and if you are expecting 100% perfection then you will struggle to accomplish your goals. Setting your team up for failure with micromanaging or interference will drive not only your team crazy, it will drive you crazy too. Delegating is designed to save you time, energy and bandwidth, taking tasks off your plate helps you, but you can also be the only factor in its failure.
Killian Hemmy, ATSG Corporation
Create defined roles and responsibilities for your leaders. This is a lesson that pays dividends when it is put into practice. I currently have five of my employees running our branch offices throughout Central America. They are bestowed with nearly limitless authority and are responsible for the employment and wellbeing of nearly 100 employees amongst all of their offices. Even before the pandemic I was never able to visit the offices as often as I would have liked. However, they have a very clear understanding of what they are supposed to do in terms of employee management, what their obligations are to our clients, and what their limits are before they have to engage corporate. These clear definitions were put in place from the beginning, modified as necessary over time, and reviewed for improvement on an ongoing basis. Without these defined roles and responsibilities managing our branch offices would have been exceedingly difficult during this pandemic.
Maintain quarterly counseling and annual performance reviews that accurately reflect efforts. This should be a desirable thing for all employees but is a necessity for anyone to whom you delegate. You have to be able to qualify and quantify their work product and their efforts. I’ve had employees in the past whom, for a variety of unacceptable excuses, I did not engage in meaningful reviews of their performance in a timely fashion. When some of them stumbled or failed in meeting their work goals it became a herculean task to get them back on track because we had to go through and review their entire work history to figure out where the wheels came off the track and then fix it. And for those who did not falter, a lack of meaningful feedback was equally damaging to the organization because it prevented us from making their efforts even more impactful to our mission.
Engender two-way trust. As I stated earlier, the trust factor is absolutely critical in being able to appropriately and effectively delegate. We as people yearn to be trusted and most people want to experience autonomy in their efforts. As leaders, we want to be able to delegate with the confidence that our trust is appropriately placed. Earlier in my career I worked for a manager, not a leader, who would give great lip service to the concept of delegated authority. However, in practice this individual would far too often “parachute” into situations before I had the opportunity to actually do my job and try and “fix” things. Inevitably this would cause issues because our approaches to solutions were different and when two solutions to the same problem were being exercised at the same time it tended to exacerbate the initial problem. The final outcome of this type of management (not leadership) was that I felt as though this individual didn’t trust me despite my exemplary record of performance. When this person made empty statements about trusting me but didn’t back it up with actions that were synonymous it made me doubt and not trust anything ever said in the future.
Clearly communicate intentions and desired outcomes. One of the things I learned in the military was “commander’s intent.” The commander’s intent is the desired outcome that is communicated to and understood by all members of the team. With a clear commander’s intent, even if your team encounters obstacles, loses communication with one another, or has to act swiftly without the time to seek approval in order to preserve momentum, they will know how to pivot or adjust their actions in order to accomplish the fundamental goal.
Take care of your people’s needs and they will take care of your work needs. Again — an old adage adapted from military usage but equally appropriate for the business world. Everyone’s life is different, and each person has a unique set of needs. This is especially relevant at this moment in our history. Take the time to figure out what your people need (Flexible work schedule so they can homeschool their kids? Full remote work because they have a high-risk family member?), what they are working for (Health insurance for their family? A steppingstone to a job in management? Extra money to pay for their children’s school?), and what they need to do their job as well as they can possibly do it. Then — make it your job to help them as much as you possibly can to meet those needs. Those efforts will not be unnoticed and their loyalty to you and the mission of your organization will be unparalleled.
Andrea Heuston, Artitudes Design
Delegating doesn’t mean giving up total control. You just need to pick your insertion points. My first employee — the office manager — didn’t work out. It was only after I fired her that I discovered she’d been embezzling from me, and the bookkeeper — who had had been my maid of honor at my wedding — was party to it, knowingly signing false expense reports. I signed a lot of checks not knowing what I was signing for. It was a lesson to learn, that I needed to be on top of finances and I couldn’t even trust somebody who I believed was my best friend. However, despite that awful experience I now delegate a lot of the company’s financial operations — the daily billing, invoicing, taxes and bookkeeping. But that doesn’t mean I’m not on top of the overall financial health of the company — I still sign every check which keeps me in touch with what’s going on and I review regular reports from the bookkeeper. This way I don’t have to worry about or waste my time on the little things, but I still haven’t given up total control. Figure out where to insert yourself in a process that will give you peace of mind but not bog you down in the little details.
Delegating and communicating go hand in hand. When you delegate, setting clear expectations and guidelines is key. You can’t just say, "here, this project’s yours, take it and run with it." We meet as a full team every Monday morning to talk about the week ahead, ongoing and upcoming client projects, assign roles and responsibilities and define time factors. We make sure everyone has a clear understanding of what’s expected, what the client expects, and the tools they need to be successful. Delegating without going through these steps can mean that you’re setting employees up for failure. It also ensures you won’t be unnecessarily pulled back into projects.
Hire smarter people than you with complementary skill sets and delegating will be easy. Don’t make the mistake I did early on — hiring people like me. One of my early hires — Michael — was intelligent, creative, driven and good with customers. When I hired him, I didn’t realize it was like looking in the mirror. And since we shared the same strengths, I always thought I knew best and wanted to direct him. I also didn’t need to duplicate my talents, I needed to hire for complementary skill sets and people who do things better than I do. When you do that, you’ll find you want to delegate as you have the confidence that they will do amazing things and you’ll want to see what they can do.
Delegating tells your team you trust them. When you micromanage employees, you send the message that you don’t trust them. When you delegate, you’re empowering them. Most likely you’ll get better results and more loyalty. Other than our weekly Monday check in and two set meetings during the week where the design team collaborates on projects, everyone manages their own schedule and workflow. After that, I don’t need to check in. I trust them to do their jobs and things will get done. Do I care when they do it? No, they may be walking their child to school, at a doctor’s appointment or doing some volunteer work during work hours and that’s totally ok as long as they are meeting their deadlines and the client is happy.
Micromanagement is not leadership, delegating is. A business coach once told me that the best business owners and CEOs divorce themselves from running the day to day. I remember thinking that’s insane, how could I possibly do that? It took my coma to make me realize he was right! Instead of me being at the center of every conversation I could be secondary or tertiary and trust my team to do their jobs. That was a big, big thing for me.
Phil Alves, Devsquad
Have trust in others but do verify before sending on work externally. This goes back to my funny story about not checking my team’s code comment. Have trust in what others are doing but if you’re ultimately going to be held accountable, you need to be sure that you checked everything over and that you explained the reasons for doing something clearly to your team.
Mentorship is very important. When you’re first delegating, you need to be a good mentor too because if you’re giving someone a task to carry out, they need the right information and education in order to do the task well.
Always remain humble. Often you’re not the best person for the task and it’s important to learn that someone else can do a better job than you. For example, although I’m a developer and coder at heart, I no longer make coding decisions for DevSquad. I hired a great CTO who decides on code and knows better than I do!
Patience. This goes back to the idea that even if it takes someone else much longer than you to complete a task, it’s essential to be patient and let them do it because it’s the most effective way for them to learn.
Don’t be a control freak when it comes to method, just focus on results. The way someone gets to or achieves a result isn’t important, the only thing to focus on is that the desired end result is achieved.