We’ve worked with a lot of CEOs, leaders, and business owners, and no matter what industry or niche someone is in, they tend to have the same few questions. That means you probably have a few of these questions on your mind right now, too!
At Elevate, we provide operations support and services, but we also believe in educating our clients and helping you expand your own skills and knowledge.
This post is packed with our professional tips and insights, as well as some powerful perspective shifts that will change the questions you ask and dramatically improve the way you feel about your success!
Do I need a bookkeeper? And other questions we’re answering
This post shares answers to these questions:
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Why is my inbox a mess even though I have help?
We’ll dig into the one thing you’re missing that keeps your inbox organized and manageable for good. -
How do I stay focused without becoming a bottleneck?
Get clear on how you can delegate more effectively and efficiently to keep things moving without having to be constantly active in every project. -
Do I really need a bookkeeper? Can’t I just give everything to my CPA at tax time?
Let’s get serious about what not having accurate books is costing you. Spoiler alert: it’s more than what it costs to outsource your bookkeeping! -
Are we focused on the right things or just doing a lot of things?
Learn our favorite way to set clear, actionable goals and measure your progress so you can clearly see your success and progress. -
Why does everyone on my team do things differently?
Turn what feels like a failure into a positive way to improve your systems and SOPs!
What makes a good business leader?
This isn’t one of our top 5 questions, but it is something that’s worth getting clear on before we get to our Q&A.
Sometimes leaders are afraid to ask questions because they fear it makes them look weak or incompetent. That couldn’t be more wrong.
Smart, capable leaders ask questions all the time.
Is there a better way to do this?
How are the talents on my team being applied to specific roles and responsibilities?
What am I not seeing here?
Asking questions and being reflective in general is one of the best ways to build a successful team and organization. When you openly ask questions and invite feedback, you teach your team to do the same. And that leads to fewer mistakes, more collaboration, and better results!
At Elevate, we are constantly reflecting on our work and asking questions. We schedule regular check-ins with our clients and our internal team to encourage clear communication. And we’re never afraid to examine a process, system, or belief to see if there are ways to improve it or do it differently.
As you read through the questions we’re answering below, invite yourself to be reflective. Know that it’s not only okay to have these questions, it makes you a better leader to ask them.
The top 5 questions business owners and CEOs are asking
Asking the right questions leads to better results. At Elevate, we love helping our clients streamline their operations to improve every area of their business.
The answers to these popular questions will help you identify areas of growth for your own organization. You may also be inspired to do things differently or try a new system!
Let’s get into these popular business questions.
Why is my inbox a mess even though I have help?
So many of our clients come to us frustrated by what feels like the impossible task of keeping their inbox organized for more than a few weeks.
A messy inbox makes everything feel more overwhelming. And it can lead to missed information and deadlines!
Having someone help with your inbox management is excellent.
But no matter who is in charge of it… what really matters is your system.
And if you're continually having inbox issues, that's a clear sign that you either don't have a system in place, OR the system you're using just isn't working.
Without a clear, customized system, it doesn't matter how much help you have… your inbox is always going to default to clutter.
You need a simple, consistent, repeatable system to manage your inbox!
And here's the best news: Inbox Zero does not have to be the goal! We want inbox clarity.
Inbox clarity means whoever manages your inbox:
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Knows exactly where each email goes and what to do with it as soon as it comes in
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Can keep your inbox organized with only a few minutes each day
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Can prioritize urgent communication and make it easy to see what needs to be done, in what order, when you scan your inbox
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Does things the same way, every time
When you give up chasing Inbox Zero (it's unattainable at the beginning for most people!) and embrace Inbox Clarity––things will improve in a hurry.
Need help managing your inbox?
We offer an Inbox Cleanup Get It Done project that will whip your inbox into shape, no matter how cluttered it is. We’ll also lay out a detailed system you and your team can follow to keep things nice and organized for years to come.
If you’re looking for an effective DIY option, we highly recommend completing our 2025 Organize Emails Challenge!
How do I stay focused without becoming a bottleneck?
As the leader, business owner, or CEO, you want to stay focused on your role and responsibilities. But every time you try to stay in your lane and zone of genius… You end up creating a bottleneck that slows everyone down and puts projects behind schedule.
This is something a lot of CEOs deal with, so we can promise you’re not alone. The answer to this question is: delegation. This is one of those easier said than done suggestions, so let's break it down.
Leave room for errors when you’re delegating.
You'll make errors in delegating at first, and the person you're delegating to will make their own mistakes. These are a learning opportunity! Whenever mistakes happen, it's the perfect time to ask questions, get clarity, and refine the process or system.
Embrace the teachable moments. Offer praise for what was done well and share tips or advice on ways to improve or make things easier.
Give ownership to whoever is doing the project.
Set milestones for check-ins so you get the info you need without having to approve each step and be actively involved. When you set milestones at the beginning, you can avoid being constantly involved in the process you're trying to hand off.
Get everything out of your head.
In the beginning, delegating is going to take a toll on your energy and time. When there are processes or systems that only live in your head or don't exist at all, it will take time to create them, document them, and teach your team or contractor how to complete them. That's okay! It's just part of the process.
Need help with delegating?
Sign up for one of our monthly Mastering Delegation Workshops or book a 1:1 call to create a customized delegating plan with Ashley, our founder and DOO.
Do I really need a bookkeeper? Can’t I just give everything to my CPA at tax time?
Technically? Yes. You can hand over everything you have to your CPA at tax time.
But what are you sending your CPA? Is any of it accurate?
If you don't have a bookkeeper managing your business's finances on a daily basis, you are missing out on:
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Accurate forecasting for the next season or quarter
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Understanding your profit
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Using your financial data to make informed decisions
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Knowing where your money is going
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Planning for client gifts, team bonuses, and holiday gifts
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Valuable write-offs
Collecting receipts is not the same as bookkeeping. If you’re simply collecting paper and digital receipts, how do you know what you're missing?
Not having accurate, updated, organized books is costing you in every area of your business.
At a minimum, you need a bookkeeping software and system you can follow in-house to keep track of your expenses.
A better option is to outsource your bookkeeping to a professional. This gives you real-time financial data to inform your business decisions and ensures you always know your profit margins, expenses, and other key info.
Need help with your bookkeeping?
Choose from our one-time Bookkeeping Clean Up or Bookkeeping Set Up Get It Done projects or invest in a bookkeeping retainer service with our team of pros!
Are we focused on the right things or just doing a lot of things?
You're probably asking this question if you:
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Regularly work overtime or on the weekends
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Feel a high level of stress at all times
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Are always working on something, but rarely seeing results
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Feel burned out, overwhelmed, or just over it all
Too many CEOs and leaders don't feel like they're making any progress because they don't know where they started or where they need to go.
Constantly working without clearly defined goals will drive you to exhaustion in a hurry. So how do you know if you're focusing on the right things?
It all starts with where you want to go and what you want to achieve. Defining clear, specific goals is the first step in knowing what you're achieving.
After you have your goals, you need KPIs (key performance indicators) to help you see how you're making progress.
And around here, we're big on celebrating progress over perfection or completion! Even if you don't reach every goal, there are wins, lessons, and value to celebrate along the way.
Setting specific goals, sharing them with your team, and tracking your progress on a daily, weekly, monthly, and quarterly basis will help you know you're doing the right things and feel more accomplished as you do them!
Need help with setting clear goals and accomplishing more?
Schedule a Strategic Mapping session! You’ll work 1:1 with our founder and DOO, Ashley, to create a goal-oriented Action Plan for the next four quarters. Having defined, specific goals is the best way to feel more in control and successful!
Why does everyone on my team do things differently?
Raise your hand if your team:
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Saves things in different places
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Shares updates across different types of communication
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Titles documents differently
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Communicates their progress in different ways
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Completes projects on different timelines
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Feels like a jumbled mess of everyone just doing their own thing
We see your raised hand and maybe even a hint of embarrassment. We get it. It feels like a good leader should know how to keep their team in line and all on the same page.
But here's the paradigm flip I want to offer you today:
Instead of a failure of leadership, it's a positive that everyone does things differently.
You're not a bad leader. You just don't have processes and systems documented and shared with your team.
But right now, while everyone is doing their own thing, it is actually the perfect time to dig in and create some SOPs (standard operating procedures).
Everyone has different brains, priorities, and perspectives. And by letting your team do things their own way, you are able to see better ways of doing things than you would have come up with on your own!
Now you just need to take stock of what's working and where things need to improve so you can create a library of SOPs everyone can follow.
Need help creating SOPs for your team?
Our operations experts love creating custom, streamlined systems. Book an SOP Library Get It Done project and we’ll deliver your defined, documented, and dependable SOPs in just a few weeks!
Am I failing at business?
This is the final question we want to address because so many talented, successful leaders and business owners are constantly struggling with this one.
No, you are not failing.
You're probably just not looking at everything you have accomplished! It's so easy to get caught in the vicious cycle of setting big goals, showing up and doing the work, achieving the goal… and then just moving on to what's next.
Can we invite you to try something different?
If you feel like you're failing (or not living up to your own high expectations), take 5 minutes right now and celebrate the wins – big or little – you've had recently.
And moving forward, make celebrating progress a non-negotiable.
You can do anything, but not everything. (That's where we come in!)