How do you manage someone with ADHD? I have someone who wants detailed instructions & expectations with multiple reminders & check-ins for deadlines. They want this for everything, even small routine weekly tasks. They often won't get the work done if this doesn't happen. I manage 20 people & have my own deliverables. I don't always have the capacity for this, and while I'm empathetic and have tried to be patient & work with them, I do need some independence from them. Any suggestions?

They seem like someone who needs a lot of confidence building and doesn’t realize the variables that are involved in the projects. I would tell them that this is a standard expectation for their role.
Screen sharing the timesheet submission is wild.. I would remind them that the LOE they’re asking of you pretty much removes the need for them in that role This sounds tough but it sounds like a lot of hard convos are needed of expectations and the support you can give.
They may need or are used to a micromanager, which you are not and cannot do.

As an adhder and a leader who has had neurodivergents on team, I sympathise.
Sometimes it cannot work out but sometimes the right support can result in a wonderful
Outcome.

Sounds like you need an intervention and support from HR. In turn they should get a work needs assessment undertaken - with Lexxic or Genius Within or whichever ND consultancy you use.
This will then identify what this employees has challenges with and what they excel at. Together you can then agree what tasks will help in building confidence and perhaps some tasks should be delegated to someone else. Or co-created.
The assessment will also then help to identify, with your input, what a reasonable adjustment might look like.
Requiring you to micro manage and break everything down may not be considered a reasonable adjustment. As these also need to be reasonable for you and your organisation, not just the individual.

A reasonable adjustment may include use of medication if the person is not already medicated. Acknowledging that meds don’t work for everyone.
Or might include different hours
Could also include some 1:1 coaching with an adhd specialist coach. Who could assist with the breaking down of a project into its constituent activities and support the individual to create their own and then meet those milestones, independent of you.

Good luck. Definitely speak to HR as this way of working is not sustainable.

Can you ask this person to set outlook reminders for himself?

Have they reported this as a disability to HR?

If not, start the PIP process and exit them out.

I think having them write out their deliverables and having you review them for gaps. I think people don’t always realize the level of work that goes into it. I use Asana and then create my own subtasks with notes so I have everything I need to look back and reference.

If there’s any way that they can come up with their own milestones and ECDs based on the final goal that you give them, I wonder if that will help with encouraging self-sufficiency

If they produce good work when accommodated, see if there is someone else who can assist you with accomodating them. I have ADHD and I work best when my needs -- including things as small as fun colored pens and specific journals -- are met. Or perhaps find a way that they can accommodate themselves. If you work together, you might be able to find ways to ease your load, empower them and produce great results.

You need to coach them to set their own systems for staying on top of deliverables. Teach them to set up calendar reminders for deadlines or self-check ins.

It’s great to recognize neurodivergence at work, but it’s not actually your job to tailor to them (short of reasonable accommodations). It’s their job to navigate and adapt.

This person wants milestones for each day and each week that they have to hit. If I give them a project that has a three month timeframe, they want it broken down into deliverables for each week. We work in agile so there is a process, but we also have dependencies on other teams and I can't control their timelines, which seems to frustrate my employee.

I've given them a breakdown of different types of projects that include milestones, usual timeframes, a checklist of tasks to get done, etc., but they seem to need a lot more than that. If I say "we need all user stories written by X date", then they'll ask how many stories need to be written and spiral if I don't have an exact number. But that's not for me to determine and it's based on the outcome of the research the team does.

We have to input time codes for each project by the end of the week. I tell the team to get them in by noon on Friday. If I don't personally remind this person every Friday, they won't get them in. I've added calendar reminders, but my employee says they need me to send them a Slack confirming they've entered their time so they're "held accountable and remember to do it". They've sometimes asked me to schedule a meeting to watch them put in their time codes so they're held accountable.

I'm trying to be patient and manage them with empathy, but I have 20 people and I feel like so much of my time is spent on this person. I feel guilty delegating some of the more admin tasks.

Are they right out of undergrad or have they been in the workforce for a while?

As someone with ADHD myself I can tell you managing someone with ADHD starts with them managing themself.

It sounds like you are providing accommodations, but there needs to be a responsibility aspect on their end. Start with suggesting really small steps they can take. It may help you to ask them what they are doing to become more independent at work (and set goals here/follow up). Their actions managing their own calendar may not be obvious to you but it may take a lot of effort for them, so recognize the effort if they are trying and make sure to give feedback often (within reason, like in a weekly 1:1, not daily. Also may help to have it written in an email so they can go back and check/review as they need to).

It may be helpful to understand WHY things don't get done (they should be doing this self reflection, but you may guide this thinking). Is it a time management issue? Is it an out of sight out of mind kind of thing? Is it a difficulty starting? Is it a lack of focus or constant distraction? Is it a lack of interest? Knowing more can help offer a targeted solution, but they need to be willing and not use ADHD as an excuse (ie. they need to learn to manage themselves for common tasks)

What about speaking to them about using calendar reminders so they can remind themselves? I personally use them quite a bit to help me with deadlines and non routine requests.

Neurodivergent people often face severe workplace burnout from what’s known as “masking” (trying to appear acceptable/normal). I have ADHD and was not diagnosed until my 30s. Dealing with this did not just require extra help from a project manager to streamline tasks and ensure I meet deadlines but also extremely specialized therapy to help me get past debilitating burnout. There is also certain kinds of work I cannot do if I’m in a noisy office.

Now, this person sounds young and like they have been diagnosed for a while, but they may need mental health treatment in addition to workplace accommodations.

I was working with someone like this. I ended up delegating managing this person to someone junior who was looking for growth and management opportunities. It’s a win-win.

I have ADHD which I handle on my own with post-its, lists, and notepads. I book appointment-time on my calendar and set up reminders to keep me ahead of the game. On busier days, I need to set my status to Away, Do Not Disturb, or Offline to get things done. This really looks like they're not on top of their condition. Maybe support them on joining a time/project management training. I loved Lean Mfg and FPX. I'm not sure if HR has other tools that would be helpful.

There are professional coaches who can help with this issue. It is part of a reasonable accommodation that will assist in performance. Coaches can be impartial third parties as a solution to identify what the struggle is and make recommendations for improvement plans, partnering with you, the person, and HR.

As far as the time tracking goes, that is a responsibility to ensure hours worked are compensated (even if the person is salary.) - which is basic responsibility of having a job. The person has the ability to set outlook reminders, and appears they have been enabled.

ADHD is an annoyance and exhausting. Finding the root of the insecurity is important to help build confidence in actual ability. But the person has to take accountability for their inaction and want to improve. Holding them accountable for milestones and asking for their plan on how to achieve the larger goals may also help to see their thought process and potentially what stifles their progress.

Hi, my husband has ADHD and works in a similar field. You’re not this person’s secretary. This colleague probably has a number of techniques they already use so they should be bringing those into the workplace. Your workplace may need to offer ‘reasonable allowances’ but it’s 50-50 on them and the workplace. You might need to ask Human Resources what are the limitations of what you can offer, as it’s affecting your day-to-day productivity.