Delegation: What Your Team Wishes You Knew

delegation team delegation

When I was in college, the words “group project” chilled me to my very core.

For someone who prefers knowing that I alone control the outcome of a project, trusting others to hold up their end wasn’t an easy thing to do. It felt so blind; maybe my teammates would do a good job, but maybe not. Maybe they wouldn’t do the work at all, and I’d be left to pick up the pieces.

Sometimes I’d throw up my hands and just take on all the work; hey, at least then it’d get done, right? Other times, I’d delegate like crazy and cross my fingers. Still, the entire process always felt a bit hellish and not conducive to putting out great work.

Growing from solo management to team collaboration

It’s an experience that probably rings true to many new entrepreneurs and small business owners.

In the beginning, it was likely just you—you were the only one running your business, making key decisions, and doing the work.

You did the whole “group project” on your own; while it may have meant a lot of late nights and gnashing of teeth, you could be confident that everything was being done to your standards, and there was never any doubt about whether or not something had been completed.

However, difficulty arises when it’s time to scale. As your business grows, you’ll inevitably need to take on more team members.

Suddenly, projects that you would have taken on all by yourself are now your responsibility to split up and assign to multiple people. Not only are you faced with the prospect of giving over control of your “baby,” but you also have limited oversight on who is doing what. You have the power and responsibility to delegate effectively—but doing so can be a challenge.

Ultimately, when work is delegated across a project team, it’s hard to know for sure if something is getting done the way you think it should be done, and whether or not it’s being accomplished in a timely manner. As small businesses grow, entrepreneurs suddenly find themselves in leadership roles, and realize that delegating work isn’t as easy as it sounds.

Why is delegation so challenging?

At its heart, delegation is trusting that the team member you assign a task to will do it as well, if not better, than you would yourself. It’s about assessing who is good at what, and the communication styles needed to bring out the best in everyone.

It can be challenging, even for seasoned leaders, but especially if you built your business from the ground up by yourself. After all, you know how things should be done—and asking someone else to take over means that they might make a mistake, or complete a task in a way that might not be up to your standards.

So, what do you do?

Well, you don’t do what I did as an undergrad: take on everything because you don’t trust others to do it right. Not only is that unsustainable, but it isn’t an effective use of your (likely highly skilled and competent!) team.

Instead, use these four strategies; they will make delegation easier to manage, and you’ll be able to trust the work is done right.

4 tips for delegating effectively

1. Get clear on communication expectations

The more clearly you define your standards and expectations, the easier it will be to hand off projects.

Spend some time thinking about what tasks you do often that you’d like to be able to entrust to others, and maybe document your own process, so you can share it with your team. Do you have a certain way that you like to speak to prospective guests or clients? Put together a best practices guide so that everyone is on the same page. If you interact with customers or clients often via email, creating an email template can be a good place to start, and can help standardize responses to commonly-asked questions. With clear documentation in place and a staff that is trained on how to implement your processes, you’ll be comfortable knowing that they’re handling everything just as you would have, regardless of the situation.

On a related note, not everyone has the same communication and work style, and having clear documentation and a dialogue with your team will enable you to figure out how to convey information effectively to everyone on your staff.

To use myself as an example, I am someone who needs written clarity in order to do my best work. For me, this looks like set deadlines, clearly laid-out expectations and scope, and regular communication about whether or not my work is meeting expectations. My worst nightmare of a project is a suggestion that I just “wing it.”

However, some team members might find the rigidity that works for me, well, rigid, and might thrive with a more loosely-defined scope, as long as they understand your end goal. (On this note, you might want to consider having your staff create their own personal user manuals, which are a great way to find out more about what works and what doesn’t work for your team as a whole.) So, clear communication doesn’t just mean documenting processes—it also means finding out what type of communication resonates with your team members.

2. Have regular check-ins with team members

It can be scary to feel in the dark about how your team is handling things. To combat this, schedule regular meetings to touch base and hear your team go over what they’re working on, and how they’re putting things into place.

The frequency with which you’ll need to do this will depend on your business, the scope of the project, and plenty of other factors; however, a weekly one-on-one meeting may be a good way to get the lay of the land from your team, and give you an opportunity to make sure projects are being completed in a timely manner, in a way you feel comfortable with. Having a meeting agenda can be helpful here; you’ll be able to stick to the topics you need to cover, and you can keep meetings on track by sticking to the outline. You might also consider asking your team to send you regular updates, so that they can keep you in the loop.

3. Find ways to have hands-off oversight

No one enjoys being micromanaged. However, thoughtfully-implemented oversight will allow you to can keep an eye on your team without micromanaging them.

Consider looking into project management tools that will help give transparency into what is being done, and how it’s being accomplished. For example, tools like Basecamp allow you to get regular updates on where your team is when it comes to a specific project. You can assign tasks big and small to your team, and you’ll be able to keep all your work in one place. Plus, project management tools like Basecamp keep a log of actions and conversations, so you can easily pop into a task and check out the status of the work.

Similarly, our product Outpost allows you to assign emails to specific team members, which makes it easier to delegate work transparently—and you won’t have to forward an email on to a team member and just sit back and hope they’ve taken care of it. You’ll also be able to keep track of what emails have been answered and which haven’t, which means you’ll be able to make sure everything is being taken care of efficiently and effectively.

4. Hire right the first time

Finally, it should go without saying that hiring team members that you can trust and whose work you know to be quality should be priority number one.

If you’re unsure about the skill set of a prospective employee, or you can’t quite tell whether or not they share your desire to cultivate a company culture that values your customers, it’s probably best to hold off until you can bring someone on that you trust completely.

Here at Palo Alto Software, we have multiple rounds of interviews, and on-paper skill set is the jumping off point, not the be-all end-all. We like to see new potential teammates in action, and what they are actually like as an employee. We also interview for culture fit, to make sure that they are the type of person who will thrive on our team.

Hiring is a gamble, but you reduce the risk a lot if you can get at the heart of whether a candidate is actually capable of doing the work (rather than simply saying that they can do the work), and whether they genuinely want to do it for your company.

The reality of business growth is a bit of a double-edged sword: The more successful your business becomes, the less control you personally have over every single thing that takes place.

However, if you use the opportunity to train your staff effectively, be smart about delegation, and find ways to maintain a healthy amount of oversight, you’ll be able to build a process with your team that works, and focus on continuing to grow and strengthen your business.

Posted in: Employees Productivity

Briana Morgaine

Briana Morgaine

Briana is a content and digital marketing specialist, editor, and writer. She enjoys discussing business, marketing, and social media, and is a big fan of the Oxford comma. Bri is a resident of Portland, Oregon, and she can be found, infrequently, on Twitter.

Further Reading

5 Tips for Managing Your Shared Mailbox Like a Pro With Outpost

If your company uses more than one shared mailbox or team email address—and most companies do—then email problems can multiply.…

Using a Shared Inbox Can Make Your Team More Productive

Setting up a few specific inboxes is the first step to getting organized and delegating email tasks with confidence. Here's how to…

How to Use Shared Inbox Rules to save time and get organized

Learn how to use rules in your shared inbox to automatically organize your email, assign emails for follow-up, and send the right reply…