Skip to content

Ask Ashley: How do I figure out what to focus on, delegate, or hire for?

My team is overwhelmed and I am being pulled in too many directions. I don't know where I should focus my time versus delegate versus hire. Help!

Ashley Janssen
Ashley Janssen
6 min read
Ask Ashley: How do I figure out what to focus on, delegate, or hire for?
Photo by Yan Krukov from Pexels

Welcome to the Ask Ashley advice column! On the second Wednesday of every month (this month it's the third because I had a timely post for last week), I answer a question from my subscribers, consulting clients, or social media followers on their biggest productivity challenges.

Have a question you want to submit for another edition of Ask Ashley? Shoot me an email. Questions will be anonymized and may be edited for clarity.


Dear Ashley,

Work has been overwhelming for my small team for a while. I know I need to hire but I am being pulled in so many directions and I’m not sure what role I should hire first. I feel like I keep getting lost in the weeds and I’m not focussing on the right things. I’m not sure what I should be delegating versus where I should be putting my own time.

How do I figure out where I should focus my time, what to delegate, and what role to hire for first?

– Tired of Tug-of-War

Dear Tired of Tug-of-War,

Your experience is a common one for so many entrepreneurs. When you are solo or have a small team, there are so many different hats to wear, all with the juggle of time, resources, and money. As you add new and larger projects and team members the complexity of your business changes exponentially.

It quickly becomes clear when it’s no longer good enough to have processes in your head and ad hoc ways of doing things. Things great dropped, forgotten, or problems start cropping up. These growing pains are normal and can be alleviated with a bit of reflection and intentional planning.

Let’s start by breaking your question down:

1. How do I figure out where I should focus my time?

This is a big question! It’s helpful to take a step back and think about it from a higher-level strategic standpoint. If you were to design your ideal role and the business that you wanted to run when you first started out, what would that look like?

Your ideal role will be your north star when you are trying to decide what to focus your time on. It’s the intersection of:

  1. What you are good at;
  2. What you enjoy doing; and
  3. What moves the needle on your business's goals (and therefore revenue).

Your ideal role is a future state that you work towards as you grow your business and think about the other two parts of your question: what to delegate and what role to hire for next.

What is your ideal role?

To figure out your ideal role, you need to be able to articulate the answers to the following:

  1. What is your role now?
  2. What do you want your role to be in the future?
  3. What don’t you want your role to be in the future?

It will be in the gap between what you are doing, what you want to be doing, and what you don’t want to be doing that you will start getting some of the answers. To get the answers to these questions, you need to dig deeper by reflecting on:

  1. What are you good at professionally?
  2. What are you not good at professionally?
  3. What do you most enjoy working on?
  4. What do you least enjoy working on?
  5. What are the high-level areas you are currently responsible for?
  6. What are the specific tasks you are responsible for?
  7. What are the things that only you know how to do?
  8. In an ideal world, what would you continue doing?
  9. What would you stop doing?
  10. What would you start doing?
  11. What are things that no one is doing that you think should be happening?
  12. What makes you excited to get up and do every day?
  13. What do you dread working on or put off because you don't want to do it?

*Note, some of these questions overlap and have similar answers. That’s intentional because it’s helpful to ask the same question in multiple ways to get to the heart of an issue.

Knowing the answers to these questions is important because being good or bad at something, or liking or not liking something, is not always an indicator of what you should or shouldn’t be doing. Just because you are good at something, doesn’t mean it’s the best use of your time and skills.

This work will help you part the clouds and shine some light on where you should spend your time.

Photo by Todd Quackenbush on Unsplash

A note about things you don’t like doing

Something to keep in mind as you go through this process is that, like any job, there will always be parts of your business and tasks that you don’t enjoy. That’s normal and just part of life.

Something to consider when you think about things you don't enjoy is:

Do you not enjoy them because you don’t know how to do them, which causes discomfort, or are they things you truly don’t like?

If it’s the former, this is an opportunity to learn, push yourself, and stretch your skills. It’s the balance of being on the edge of discomfort (which is where you learn the most) versus hating something.

There are also things that you might not enjoy, but that are really important for you to have at least some knowledge of. For example, I have many clients that loathe dealing with their cash flow, but it is a vital part of their business knowledge, so they force themselves to work through it.

2. How do I figure out what to delegate?

When you know what you are good at, what you enjoy, and how they contribute to your business growth and revenue, you can look at what's left. Everything else is the tasks you should delegate and the roles that need to be filled.

The opportunity here is to first look within your existing team for skills and knowledge to take over tasks and roles before deciding what roles to hire for.

As mentioned, in small teams everyone is usually wearing multiple hats. Often tasks and roles are organically taken over when the need arises, but sometimes the best person for the job isn’t necessarily the one who does it.

Get each of your team members to go through the ideal role questions that you did. It will help:

  1. Get them to reflect on the best use of their skills and talents.
  2. Make them feel more involved in the direction of their role as the company grows.
  3. Identify areas for education and skill development.
  4. Identify tasks and roles that are better suited for others.

This comes down to having the right people, on the right bus, in the right seats (from Jim Collin’s book, Good to Great).

Photo by Ant Rozetsky on Unsplash

3. How do I figure out what role to hire first?

After working through the ideal role question yourself and with the current members of your team, a clearer picture of the skills gaps in your business will have emerged. You will have a better idea of the types of tasks or roles that:

  1. Someone is doing but you need more of those skills for the volume of work;
  2. Someone is doing but they are not best suited for it; or
  3. No one is doing it at all.

There will likely be multiple roles that you want to hire for that help with the growth of your business. If you can only choose one (because you can only afford one at this time, for example), the questions to ask is:

What role will provide the biggest bang for your buck?

There will be a variety of factors to consider that are specific to your situation that will influence the answer to this. Things like:

  • Cost - What level of salary does this position require?
  • Amount of current work planned  - Do we have enough upcoming work in our pipeline for this person?
  • Availability in Market - Is this position easy to fill in the current market?
  • Billable/revenue producing - Is this position highly billable/produces revenue?
  • Training - Is someone available in the department for training?
  • Processes  - Are the processes for this position well-documented?

When you work through deciding which role to go forward with, try using a decision matrix. I have an entire post, with an example for hiring specifically, that walks you through how to do one.  


There are a lot of moving parts to manage as you build a business. It’s exciting to grow and add new projects and team members but they add complexity and it’s easy to get caught up in the day-to-day, jump from fire to fire and not necessarily know what to prioritize when everything feels like a priority.

Not to worry! Take a breather and get some clarity on where your skills are best allocated, do the same for your team, look at what you need to reach your goals, and then hire for what’s left.

The answers to the ideal role questions will change over time for you and your team as everyone develops new skills and matures. Go through this process a few times a year to make sure you are aiming your efforts towards your north star and doing what’s right for you and your business!

Do you need help working figuring out your ideal role? Book a free consultation to chat about it!

Ask AshleyStrategy
Ashley Janssen

Ashley Janssen

Productivity consultant, writer, speaker, serial entrepreneur, chaos calmer, introvert, cat-lady. Lover of books, fitness, old fashioned’s, basketball, and video games.

Follow me on Twitter, and LinkedIn.


Related Posts

Why Overplanning Is a Trap And How to Stop

I love a good plan but it can easily become a crutch that prevents you from just doing. Learn 5 strategies to stop overplanning and get started!

Why Overplanning Is a Trap And How to Stop

Ask Ashley: How do I set my vacation up for success?

Learn 5 strategies to follow in the weeks leading up to a vacation to set it (and your return!) up for success.

Ask Ashley: How do I set my vacation up for success?

9 Ways to Get More Out of Networking by Being Intentional

Networking events don’t have to be terrible. Learn how to take a more intentional approach to how you spend your networking time.

9 Ways to Get More Out of Networking by Being Intentional
Subscribe