If you look like a leader and talk like a leader...
May 3, 2012 10:20 AM   Subscribe

I'm the new supervisor for a director who needs to develop more director-level skills: project management, leadership, taking initiative. Can you recommend concrete things he might do so I can help him show measurable progress?

I was asked by my boss to supervise and evaluate another director, who manages data and information systems for our small nonprofit. My boss and I are both new here, but the director of information systems has been here for more than a decade.

Long story short, he's comfortable enough with the technical aspects of the job, but previous managers have not encouraged him to show initiative or make suggestions, so a lot of the director-level instincts he might have had have been trained right out of him. He's also received generally positive evaluations under previous regimes, perhaps because no one knew enough about information systems or wanted to deal with the management hassle of mentoring an employee who needs guidance.

Are we storing information in the best, most organized way? Are we using the best constituent database for us or should we get a new one? What additional reporting do we need to develop in order to track and compare our fundraising efforts? These are all questions I might expect a director to ask and answer, but he finds this kind of thinking very daunting.

I have given him an evaluation which says positive things about some of his work, but that he needs to improve the skills that would actually make him valuable as a director. So, I need to be able to show him how to make tangible progress in intangible areas, some of which make him uncomfortable (because he's internalized that previous bosses don't want him to show initiative).

We'll re-evaluate in 90 days; what can I do to give him a fair shot at improving? I know leadership when I see it but I need help conceptualizing goals in a way that helps him see it too.
posted by anonymous to Work & Money (8 answers total) 26 users marked this as a favorite
Put him through PMP certification. Like an MBA or law school, getting your PMP cert fundamentally rewires the way you work, and much for the better.
posted by mhoye at 10:24 AM on May 3, 2012 [2 favorites]

No, no, no. He's a director, it's _his_ job to know where he can identify places to show leadership. Don't do his job for him. Have him sit down and brainstorm with you different projects or deliverables that can show leadership. He knows the area, he should know better than you. Pick 3, slap a deadline on it, and make him responsible for regularly reporting to you on progress.

Uncomfortable is _good_. Uncomfortable means he's growing.
posted by bfranklin at 10:24 AM on May 3, 2012 [2 favorites]

I agree, PMP Certification is a place to start. It's expensive though, although I did my coursework on-line via Gerogia Perimeter College for about $400.

The Certification test is really pricy though and if the non-profit won't pay for it, that might not work out so well.

I would write out a list of behaviors that demonstrate the skills you expect, that you aren't seeing now:

1. Holding weekly staff meetings

2. Training those that report to him.

3. Creating a list of projects with expected time-frames and results that he'd like to initiate.

Perhaps he can attend a conference or participate in a users group? These are good places to start.
posted by Ruthless Bunny at 10:33 AM on May 3, 2012

Manager Tools has an excellent series of free podcasts, and a number of them specifically address coaching (look for "coaching" in the title). These may not give you the exact goals that you will set, but they do give you the template for any coachable goal. They very clearly lay out their coaching model and specific steps to start using it, and in later podcasts they answer questions and provide examples. I strongly recommend that you listen to these podcasts - they might be all you need.

For example, any goal (and its improvement) must be measurable. "Better Project Management" is not a coachable goal; how do you measure that? But you can measure better communication ("sends a weekly status updates to stakeholders on time every week"), better planning ("provides a detailed project plan with deadlines for any project requiring over 150 hours of work"), better execution ("team meets deadlines on 80% of projects"), and better delegation ("delegates 4 low-priority tasks to team every month"). You then measure these weekly - did the weekly report go out on time? Did he provide a project plan?

I'm not sure about measuring the "taking initiative" part since I'm not a director, but maybe it would be something like this: "submits a proposal to improve IT services once every 6 months." Then you can coach him through drafts of that proposal. If he's not used to this kind of thinking then he might find it onerous at first, but coaching him through such a proposal might help him understand the kind of thinking that you and your boss are looking for. And making it a report means he won't feel ambushed like he would if you ask him this in a meeting. It gives him time to think and digest and go through a few drafts while he learns how to think this way.

As the Manager Tools guys point out, you don't have to teach all (or any) of these skills. A coach is not a teacher. But you might set some goals and get baselines, then send him to training (PMP? Leadership skills? IT/operations strategy courses?) so he knows why he's going to training. When he's done with the training, you start measuring his improvement towards the goal and provide feedback, but that's very different from teaching him everything.
posted by Tehhund at 11:18 AM on May 3, 2012 [2 favorites]

You also might want to think about whether there are styles of leadership that play to his strengths.

So, for instance, maybe confronting ambiguous, open-ended questions is very daunting - but maybe he'd be a whiz at preparing a thorough assessment of industry best-practices, and then pushing that report through a documented governance structure (this committee from my own group vets it and chooses 3 recommendations, then I narrow it to 2, then it goes to my boss's boss for a final decision.) Maybe he'd be great at defining and displaying performance metrics in areas you currently aren't measuring. Maybe he'd be good at 'reality checking' other people's project plans for technical feasibility.

Not that he won't need to develop some new skills, but he'll be in a much better place if you can also show him how his existing skills can translate into leadership behaviors.
posted by Ausamor at 11:24 AM on May 3, 2012

I think there are two things going on here. Answers like PMP training are more about the mechanics of management, but the questions in the post like "Are we using the best X?" are questions of vision. If that's what you want, help him identify the areas where you expect him to have a vision and set him on the task. I've had good managers that do one or the other of this well, but the best can do them both.
posted by advicepig at 12:13 PM on May 3, 2012 [1 favorite]

It's also worth noting that I would never expect my IT director to tell me what should be in a fundraising report. That's development's job. IT should help guide them into making a good technology decision to support the business case.
posted by advicepig at 12:15 PM on May 3, 2012

Your expectations around long-term direction-setting, project management, staff management, etc. should really be institutionalized by people at your level via deadlines for an annual departmental workplan, project timelines, annual staff reviews, etc. This will show him and all the other mid-level managers what you want from them and create the context for teaching him what you want.

Most people learn by doing. If he's been scared off, it might help to have him start with something small that can garner him positive feedback, then build from there. Rather than sending him to classes or criticizing him, I'd coach him through whatever you actually need from him as a director right now, starting with something small. I'm assuming your issue is that you want him to take more leadership of the department's budget. Here's an example:

Start with a small thing -- "We have a small surplus for infrastructure upgrades and would like to allocate approximately $1500 next month for hardware or software improvements in the tech department. Where do you think that money should go?" [listen] "That makes good sense. Can you write that up in a two-page memo for us to take to the Board? The Board doesn't need to know the technical details, just what it will achieve for the organization and why you think it should be our top priority now. I'll send you a template for the memo." Coach him on how to express his ideas. If he suggests 2-3 ideas, suggest that the memo outline the choices and their pros and cons, but make a recommendation. If he says "$1500? What we really need is $4000 for a new server," then encourage him to make the case and then work with him to advocate for an increase in the budget. The goal here is to give him an experience where his voice gets heard, he gets praise for showing leadership, and he receives a tangible improvement that makes his department run better.

Then build up to an assignment you're giving everyone as part of institutionalizing the kind of department-level leadership you want from your managers -- "Great job with the server memo, Bob. Ready for Round Two? I have to put together our annual organizational budget and need to know what investments we should plan for in IT in 2013. So, you got that server: what's next on your wish list? I'd actually like to know what you think we need to do to have a really solid department here. We probably can't fund it all, but that list will also help us put together fundraising proposals. So, can you get me a draft list by next week, and then we can start to prioritize it?" Then, after he gets a few ideas down on paper, talk to him about it. "This list is great, but it should probably be organized by what your department's main goals are. Do you guys have a list of those goals? 'Ensure that network data is safe, support the fundraising team in tracking contacts with donors, keeping the website up, facilitate off-site access to data...' that sort of thing? It seems like #1 and #3 here are about data, #2 is about the website... Can you organize these under headings for me by next week?"
posted by salvia at 7:18 PM on May 3, 2012

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