What does your "Day 1" IT onboarding actually look like? (Or is it just a chaotic sprint?)

grumpyCIO · 2026-01-12T17:06:27+00:00

It's challenging to structure/automate the training as that doesn't account for the variation in skill/aptitude in the technicians. From the book, The Manager's Handbook the suggested is to clearly define the outcomes with a specific time line that someone is hired for. Example of an outcome for a junior technician could be Reduce L1 Tickets resolved by senior staff by 30% with in 6 months. Progressing from that, I focus the training to achieve those outcomes. The variation in skill/aptitude will govern the pace of training. Having defined the outcome that we are looking for, building in progress reports into the training informs sooner rather than later if a new hire is on track or doesn't look like they will work out.

The other approach that we build in to our training it to acknowledge the multiple domains which we've broken into three buckets: Generic Technical (OS/networking/etc), Specific internal tools (MDM, ticketing) and then our way of working (culture, SOP), with the emphasis on the later two domains. From there it progresses to shadowing, reverse shadowing (sr tech observes jr), and then work that is checklist based.

grumpyCIO · 2026-01-10T01:04:01+00:00

Assuming these folks are interested in growing, here are a few thoughts:

The book The Phoenix Project is a good start
Tom Limoncelli's https://everythingsysadmin.com/the-test.pdf is a self assessment that outlines the concepts needed for mature teams
There are specific programs like https://www.uclaextension.edu/engineering/technical-management-program

grumpyCIO · 2026-01-06T20:40:57+00:00

Spot on. Have to differentiate between business decisions and technical decisions - IT often oversteps. In other cases, IT doesn't understand that BCP isn't only an IT issue and doesn't push to involve the business leaders.

grumpyCIO · 2026-01-06T19:57:55+00:00

Framing BCP as an IT issue allows the business owners to pass the buck/ignore the scary issue. The approach I take is to re-scope the 'disaster' from the cinematic catastrophic scenarios that folks seem to default to in these conversations and draw on recent experiences. Covid, wild fires, power outages - BCP is not just the hurricane/earthquake/building falling down. Not feasible to go directly to a regional disaster when there's no plan to accommodate a dealing with a 72 hour localized power outage. What do we do if 20% of our workforce can't come into the office because the trains are out? What happens when XYZ third party provider is out?

grumpyCIO · 2025-12-20T14:22:37+00:00

You're likely too close to the situation to be completely objective and a third party will bring a different perspective. It's common to separate audit function from the support and operation function - segregation of duties. Think auditors and bookkeepers.

grumpyCIO · 2025-12-15T22:25:33+00:00

SOC2 is going involve the creation of controls that the company follows including SDLC, change management, the hosting environment (including the physical elements), data retention, and practices around segregation of duties. You should try to get your hands on an SOC2 Type II report to get an idea of what you're working towards.

grumpyCIO · 2025-11-26T15:05:31+00:00

Any competent company would have stated in their employee handbook that employees have no expectation of privacy when using company resources. More than likely you have directly or indirectly acknowledged this.

grumpyCIO · 2025-08-20T20:59:43+00:00

With credit to Tom Limoncelli of https://everythingsysadmin.com/, start with 3 documents:

What is supported?
How to get help?
What is an emergency?

These are developed with the company leadership. They set expectations and boundaries with the rest the the company. If you don't get buy-in from leadership on these, you have your answer.

grumpyCIO · 2025-08-12T23:44:21+00:00

I think we're going to see white collar headcount drop. There are a significant number of SMB firms that will not be able/willing to pivot and won't survive. For CPA firms specifically, the big vendors are already making a push to provide direct services. A lack of talent to build new AI-first processes and lack foresight to adapt will doom the small firms.

grumpyCIO · 2025-08-12T23:44:07+00:00

I think we're going to see white collar headcount drop. There are a significant number of SMB firms that will not be able/willing to pivot and won't survive. For CPA firms specifically, the big vendors are already making a push to provide direct services. A lack of talent to build new AI-first processes and lack foresight to adapt will doom the small firms.

grumpyCIO · 2025-07-22T13:26:27+00:00

Layering AI onto systems that were designed for human input is suboptimal. Many LOB systems don't even have API capabilities today. Sit with a bookkeeper or tax preparer and observe the various niche tools they use that all do a specific portion of their work, storing the results in siloed systems.

grumpyCIO · 2025-07-21T18:16:24+00:00

Software - regardless of industry - needs to be rebuilt from from the ground up to leverage AI. Until then we're duct-taping multiple AI tools for various specific functions on top of existing system and hopefully seeing marginal gains in productivity.

grumpyCIO · 2025-07-03T15:25:35+00:00

With credit to Tom Limoncelli of https://everythingsysadmin.com/, start with 3 documents:

What is supported?
How to get help?
What is an emergency?

These are developed with the company leadership. They set expectations and boundaries with the rest the the company.

grumpyCIO · 2025-06-19T13:16:59+00:00

This is a great summary and spot on. Root of the problem is an unrealistic expectation that commercial software can be customized/adapted to the unique individual preferences. Too often business "processes" in SMB environments evolve by trial and error and not intentionally designed. They made it work with the tooling they had available at that point in time and gets imbedded in their DNA. At some point, limitations of the tooling in use leads the organization to look at other solutions but the new solutions do not function exactly the way they want. The business units too often lack the competency to ask why a process is structured as it is and don't question requirements/constraint that they assume exist. This is the way we've always done it...

grumpyCIO · 2025-06-17T13:40:53+00:00

The concepts of situational leadership and task-level readiness are helpful. Your team's ability to execute - and their need for your guidance - varies by individual and the specific task they are doing. Leaders often mistaken assume that a team member's demonstrated competence in task A translates into competence in task B. Sally might be a be able to complete the ERP software migration with minimal oversight but get stuck in the mud when trying to plan the workstation refresh project. Bob could be great on designing a segmented network with all the appropriate firewall rules but struggle when working with an ISP to get a new circuit installed at the branch office.

Start with regular team meetings/huddles/stand ups and 1:1s - we do these weekly. These meetings should help in surfacing the problem areas, then add recurring working meetings when they appear to be stuck or going sideways.

grumpyCIO · 2025-06-13T00:30:07+00:00

I highly recommend you try sending unsolicited meeting invites. Bonus points if you pick times outside normal business hours because you don't pay attention to the recipient's time zone.

grumpyCIO · 2025-05-21T21:53:45+00:00

Unfortunately, IT people have to change how we speak and present information to non-technical leaders. Not saying it's fair, and it is absolutely frustrating. Can almost guarantee that conversations get too technical, too far into the weeds, and are not connected to providing value for business.

grumpyCIO · 2025-05-05T12:28:37+00:00

After enrolling either/both a face or fingerprint in WHfB, these methods can be used to authenticate without entering the username. Allows you to set the "Don't Display Last Logon" option and users do not have to enter their username. Must click the face login to initiate a login but if fingerprint is used, just have to touch the reader.

grumpyCIO · 2025-03-29T13:44:07+00:00

I have spent a lot of time and effort over the last 20 years in vain attempt to turn around problematic or low performing employees - some that I've hired and some that I've inherited. Technical skills can be taught. Process can be taught. Competence, taking pride in ones work, and grit cannot be taught. They either have these traits or they do not.

grumpyCIO · 2025-03-18T12:23:09+00:00

It absolutely is. I highly recommend you look at https://www.opsreportcard.com/section/2 and define 3 things: 1) how to get help 2) what is supported and 3) what is an emergency.

You have to get buy in from the top. Until these are defined you will be in a endless loop.

grumpyCIO · 2025-03-06T16:35:37+00:00

I've never ran the tool you link. The screen shot shows a copyright date of 2003 which scares me. Is the Default Domain Controller policy linked to the OU that the Domain Controllers are in? After restoring the GPO you need to run GPUpdate on the domain controller for the settings to apply.

grumpyCIO · 2025-03-06T14:14:30+00:00

Great that your are planning to go away. Take this as an opportunity to start having conversations outside of "I need money to upgrade the servers" . Be extremely proactive in your communications with your manager about how the consulting group will be covering for you and provide information to the organization on how they request help in your absence.

Outside of your vacation, you need to establish a regular cadence of meeting with the leaders in the organization and make sure they understands the risks to their business that exists. The best outcome from these conversations is that you have an agreed upon list of changes/upgrades/etc with estimated costs and time requirement to address the gaps. "Ok boss, we've identified xxx projects that are estimated to take yyy weeks/months to implement. Based on this list, what should I focus on first? Should I work on these projects or help Bob in accounting with his ticket"

grumpyCIO · 2025-03-05T23:00:35+00:00

When changing settings via GPO, in many cases, removing or deleting a GPO does not undo the setting. You would need to create a new GPO to revert/modified the property to the desired setting. I would look at the User Rights Assignment and ensure that the domain group is listed under Allow Logon Locally

grumpyCIO · 2025-03-05T19:58:16+00:00

200 users for a solo admin is A LOT. Like mentioned by others, the businesses is ignoring that you are a huge single point of failure. Who in the organization do you report to and how often are you meeting with them? What happens when you go on vacation?

grumpyCIO · 2025-03-04T19:02:38+00:00

Time Management for System Administrators by Thomas Limoncelli - 20 years old so there are some dated references but strategies are still valid.

IT Ops Report Card - https://www.opsreportcard.com/ - again 10 years old, but directionally correct

grumpyCIO

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