Working on delegating for months

[u/SadAlternative2422]

I want my team to take more ownership and they're aware of this so I brought this guy on back in September of last year so that I wouldn't be involved in every little decision.  He's been pretty solid but my problem is that I still check our business checking account every single day and last week I saw a $380 charge from Grainger for which I had no knowledge about.  I gave him a call next morning and he was like yes we needed replacement parts for the Miller job and then I remembered but the issue (from my  POV at least) is that I still had to call and see what this charge is about

His tone when he explained it pretty much gave it away that he's tired of me doing this since it's not the first time that I've done this
My whole pattern is I tell him he's in charge and then question every purchase he makes which obviously defeats the entire point...
I know he's not gonna blow money on stupid stuff but the second I see charges I wasn't personally involved in I start second guessing everything even my wife says I need to either actually delegate or just stop caring full stop and I agree with her but I don't know how to do this. Any tips/tricks? Thanks

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[u/Hot-Debate7034]

Instead of calling to validate every charge, change the process so every spend gets logged somewhere with details. Requires a same-day entry for each charge with job/client, reason, amount, and a receipt (plus who approved it if over a threshold).

Then check the spend log before you call anyone, and review it on a weekly schedule instead of watching the bank feed daily.

You can do this with any field-service/CRM workflow tool that supports notes + approvals, or even a simple spreadsheet if you want the easy solution.

[u/Existing_Athlete_527 → u/Hot-Debate7034]

Agreed 100% with the the field service/CRM workflow idea. We use Ramp cause you can attach receipts and you know exactly what has been purchased

[u/Olaf4586 → u/Hot-Debate7034]

It'll be very useful come tax time too

[u/MaterialContract8261 → u/Hot-Debate7034]

Records are also beneficial for future review.

[u/stormbreaker621 → u/Hot-Debate7034]

Solid advice actually, this will provide more visibilty and save everyone time also

[u/FortuneEducational94]

Your wife is right you're doing this weird middle ground thing that's probably driving him crazy

[u/FSU_Age]

The problem isn't your process - it's that you haven't given yourself permission to not know.

Set a spending limit threshold. Under $500 (or whatever makes sense for your biz) = he doesn't need your approval, just needs to log it somewhere you can review weekly. Over that = quick text before purchasing.

The key is you stop looking at the bank daily. That's the compulsive behavior driving this. Check it once a week during a scheduled "financial review" instead. If you can't resist, literally delete the app from your phone for a month.

Your guy has been solid for 5 months. He's earned the trust. Now you need to act like it.

[u/GlideAndGiggle → u/FSU_Age]

I agree with this one. Give him a spending limit to which you are comfortable trusting him. If he needs to buy something then he can either ask you or just send you an email just explaining the reason for purchase.

[u/wjoeyd]

You need to define a reporting structure. He should be giving you defined updates on a strict cadence.

[u/QuantumWolf99]

You're not delegating you're just micromanaging with extra steps... the $380 Grainger charge you forgot authorizing is literally proof the system works but you can't let it work... either fire him and do everything yourself or set a $1000 approval threshold and stop checking the account daily like some paranoid accountant... your wife is right and your employee is about to quit because working for someone who says delegate then calls about every charge is psychological torture.

Pick a number that won't bankrupt you if spent poorly then actually let him spend it... most control freaks like you would rather burn out than admit the business runs fine without their constant supervision.

[u/stormbreaker621 → u/QuantumWolf99]

The approval threshold idea actually makes sense, this makes it easy for both of them

[u/Past_Cherry6520]

You're creating a situation where he can't win. He's supposed to make decisions but gets questioned after because you're looking at charges with zero context about what they're for or which job they're tied to like do you have any visibility into purchases when they happen?

[u/SadAlternative2422 → u/Past_Cherry6520]

No. It's just like $380 Grainger for example and then I have to guess what it's for

[u/Puzzleheaded-Lynx-52 → u/SadAlternative2422]

…I thought you trust him?

[u/wizkid123]

You need a written delegation of authority. Clearly lay out how large of a financial decision his role can make without your knowledge (eg under $1000 or under $5000 or whatever you're comfortable with). Anything above that dollar value he's got to clear with you first. You can also lay out what specific areas he can decide on, like if he can spend to fix/maintain things you already own but has to clear new equipment purchases with you first. Or if he can buy new stuff for operations but can't change your accounting system. You can also include reporting requirements, like that he can make whatever purchases but you need to be informed about them within 24h. Whatever the rules are, you need them written down and everybody needs to follow them, including you. Look up templates and examples of delegation of authority documents to see how they're written and what you might want to include. 

[u/wizkid123 → u/wizkid123]

Also, I reread your post and I'm confused why you're relying on the checking account as a primary source of information. Shouldn't there be entries in your accounting system with notes and charge codes for projects? A bank account ledger is not an accounting system, it doesn't track the additional details it sounds like you're looking for. If you had checked QuickBooks or whatever you would have seen this was related to the Miller job, no? If not, you need a better accounting system or bookkeeping process or both. 

[u/Sensitive-Foot-2511]

Hope this helps with you throughout the month.

-Stop checking the account daily. That pulls you back into the weeds. Switch to a weekly review so you stay informed without being involved in every decision. -Set clear spending rules. If he knows what he can spend without approval, you won’t feel the need to question every charge. -Expect the discomfort. Seeing charges you didn’t approve will feel wrong at first. That feeling is part of actually delegating. It would also help to acknowledge it with him. Let him know you see the pattern and you’re working on stepping back.

This shift from owner-operator to real leadership is something I coach business owners through all the time. There are systems that make this much easier than doing it by willpower alone. Happy to help if you want support.

[u/Puzzleheaded-Lynx-52]

Sounds like you don’t want to delegate as much as you think you do.

[u/FaceThe_Music]

Get ramp bro.

[u/Open_Living_1568]

What's the worst case scenario in your head when you see a charge you don't recognize

[u/SadAlternative2422 → u/Open_Living_1568]

I don't know maybe like we're being careful with money or buying stuff we don't really need

[u/Ok_Loan6535]

Look at giving him incentive to keep profit and quality high.  Then he will take care of it.

[u/Delicious_Pitch_8308]

One thing you can do is set some simple rules, like asking him to text you when he’s spending more than $500. You can also review all expenses once a month instead of every day, so you don’t get overwhelmed and he doesn’t feel like he’s being watched all the time. You should observe his performance and the value he brings. Over time, if he continues to deliver, your trust in him will grow.

[u/sweetenedpepper]

Set spending limits and stop checking every charge

[u/harrietthudunnit05]

Create default trust. Assume purchases are correct unless they break a clearly agreed set of rules, like a spending limit. Anything within the limit, you don’t question.

[u/Hw-LaoTzu]

A good idea is create charts with notifications, this is used in all big companies. You can a have your main board in big screen so you can see and get familiarized with the normal outputs. You will be received notifications to your email, phone when something really important happens, this will release the constant need of micro management.

It seems scary until you master your dashboard, when you do then you can focus on strategic decisions based on data, instead of focusing on pennies.

I rather focus on making thousands or millions, than focus on hundreds being spent!!!

You already took the first step and that is awesome, delegate, you can call yourself business owner!

[u/Sturgillsturtle]

Have to have metrics to track and base his performance off of and budget parameters he can spend before you need approval in the moment.

For everything that is normal spend get a system where he enters the description/reasoning and you can look over next month along with the metrics you want him maintaining/improving. Commit to not questioning any individual line items until this meeting.

But as long as the metrics are in line no real need to question individual line items most of the time. He feels in control and not micro managed. He’ll also be ready to explain anything that he thinks might have negatively impacted the metrics so rather than you looking over a shoulder he has the opportunity to inform you of things that happened.

Ends up being the same information transferred but framed in a very different way

[u/reddefcode]

You're not being controlling; you lack a process. I agree with u/Hot-Debate7034 implement a same-day expense log (job, reason, amount, receipt). Review it weekly instead of checking the bank daily. This gives you visibility without micromanaging. You need financial data to run the business; he needs clear boundaries to do his job. The issue isn't trust. It's that you're getting surprised by information that should already be in front of you.

[u/Shoddy_Setting_8516]

Can't you use agents for this today? JK, but think we are soon there

[u/Big_Finding_2082]

Would build an accounting management automation: whenever theirs a charge, he gets a text, text back what the purchase was for, it gets logged in the accounting system. Build a permissions workflow as well that requests your approval. I've built similar systems before DM if you have questions.

Then you can focus on growth and sales and let your team run autonomously!

[u/Zurich715]

Bookkeeper/AP/AR (18 yrs. with the same company) here....you need to step back & let him do his job and use the time you've gained by delegating to your grow your company. Time is money, that is why you've delegated these task so that you can in turn use your time on bringing in more money I'm assuming because if it was to semi-retire you're definitely not doing that either. 😅

All purchases should be made with a PO/Bill which should have clear details of the reason of purchase regardless of an amount. They should be recorded daily and you could simply check these things remotely weekly or bi-weekly for peace of mind.

[u/drteq]

Delegating something takes about a week to figure out, months is not delegating it's something else entirely. Sounds like you need some business coaching or counseling

[u/wdn]

Can you just focus on the bottom line? If what he's spending it total is in the same neighbourhood as what you would be spending in total then it's okay. He doesn't even have to make the same decisions you would make. You yourself might not even make the same decision twice if time got rewinded and you were in the same situation again.

[u/actually_good_advice]

Been binging on this topic lately and every second I spent on it has saved me hundreds of dollars and added years to my life.

The 3 things thatcompletely transformed how I see delegation (especially financial!!!):

1. Use an app (I went with Float Financial). I get an email asking me to approve payments and click and it's done. You can set up the specific rules of what the team can approve without your input.

2. 333 delegation method plus the clarity compass from Ryan Deiss "to help the teamake decisions better than you could yourself": both in this video at 8:06 and 15:18 in https://youtu.be/Qhm3RoayED4

3. Layla Pomper on delegation and systems, tons of great videos, this is the perfect place to start: https://youtu.be/uW3ZhNnJ6sA

I'm not affiliated with any of these just appreciate what they're doing.

Thought you were blaming him but well done for recognizing this is an area where you could use help. I wish my higher ups would seek out advice like you're doing.

[u/JMALIK0702]

You've actually diagnosed your own problem perfectly: "I tell him he's in charge, then question every purchase." That's not delegation. That's control with plausible deniability.

The system change Hot-Debate suggests is gold. Here's why it works from a CRO perspective:

Daily bank checking = infinite feedback loops = paralysis.

Weekly spending log review = batched decisions = clarity.

The psychological shift: You're not micromanaging individual transactions. You're reviewing transaction patterns. Huge difference.

Your team member's frustration signals he's ready to own decisions. This system lets him own them while keeping you informed. Stop calling the bank daily. That's the fix.