CXO Tech & Work

10 ways to help get a new IT leader up to speed

Getting used to working with a new boss, and familiarizing them with your environment can be a daunting challenge. Here are 10 ways to help you to help them get up and running.

Image: iStock/Jacob Ammentorp Lund

I wrote a little while back about 10 tips for new IT leaders which contained advice for new bosses on how best to become acquainted with their new environments and staff.

As someone who has had over a dozen bosses in the IT realm, many of whom arrived after me, I've had some experience with the flip side: helping a new manager become as effective as possible so they can be successful in their new position. Enabling the development of a strong leader by helping them obtain the information they need to know and work with is beneficial to the organization, the department and your individual goals so it's a win-win for all sides.

Building a great working relationship right off the bat can also help you demonstrate your value in your role and align your objectives with that of your new boss or work out areas where you approach things differently to find and work on common ground. This is especially important for those of us employed in IT, since unlike most other professions you may well be on the phone with (or working alongside) them in critical situations at 2 a.m. when stress levels are high and a good partnership and mutual trust is essential.

1. Serve as a resource

Be available as needed to help guide your new boss on the systems and technology, documentation, policies, and other elements that keep your department running. This is a good opportunity to help demonstrate your strengths and find areas of similarity/disparity with new leader to establish a road map going forward.

Your boss will likely start out with a steady stream of questions and requests for information, so plan to set aside a good portion of each day to handle these in a timely manner. Other fires burning elsewhere (and there always will be in IT) can wait, since making your boss effective will help reduce the incidence of those fires in the long run.

2. Offer an insider's perspective

Spend some time with your boss going over the inside details of the company; who's who, the pros and cons of various departments and personnel, and the strengths and weaknesses of various processes. This should not be seen as an avenue to point out good guys versus bad guys (there are usually both types in any given company) but rather to provide a roadmap for navigating employee relations which will help your department down the road.

For instance, give a heads up if the head of finance is nitpicky about purchase justification so the new boss will understand the importance of providing him or her with elaborate detail when submitted requests, or identify the development manager who is more aligned with your goals so they can be seen as a resource for building bridges between departments.

SEE: Policy pack: Guidelines for new hires (Tech Pro Research)

3. Don't erase or revise the past

When an old boss leaves it can be tempting to scrape off the board planned tasks/projects which are, shall we say, less than inspiring. It's not a good idea to wipe the slate clean, however, since the need or request which spurred that planned work will likely still be there and the work will just pop back onto the schedule again.

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Instead of sweeping this stuff under the rug, explain to your new boss why it's problematic or will bring less value to the organization than expected. If it will detract from more meaningful work, make sure to explain why and how. This can help establish your level of knowledge regarding departmental priorities and where the focus should lie.

4. Provide a list of current tech challenges with recommended solutions

Go over what you're facing both individually, department-wise and on a company-wide basis in terms of difficulties or challenges. Maybe systems are too outdated, there are too many interruptions and drive-by visits from users, an ineffective process such as a faulty or subpar script is causing work outages, or time tracking operations are too cumbersome. You might have issues with lackluster vendors, poor support, or a problem meeting deliverables due to staffing considerations which warrant discussion and further analysis.

Complaints on their own are not as helpful as constructive ideas on how to alleviate issues. Don't be reluctant to provide criticism of the environment, department, company so long as you back it up with a "here's what we should be doing instead and why" alternative.

Make sure you also discuss the things you enjoy or are working well to emphasize the good along with the bad.

5. Provide a list of current projects and goals with objectives and milestones

Here is where the rubber meets the road in getting a new boss oriented; go over what you're working on and what your goals are with these endeavors, as well as how they fit into the overall big picture both for the department and the company. They will likely bring some of their own goals and expectations to the table, either what they've arrived with on their own or those which have been handed down from upper management.

Expect some adjustment and course correction as your new boss may have differing priorities or a specific focus as emphasized by higher-ups. For instance, while break-fix work is dull and dreary (albeit necessary - mostly) will undoubtedly end up on the agenda, like it or not, rolling out new systems and services or improvements to existing ones offers better a organizational advantage which most new leaders will want to leverage to help establish credibility and a can-do spirit.

SEE: Tips for building and advancing your leadership career (free PDF) (TechRepublic)

6. Don't be afraid to ask for more resources

Don't act as if you can do it all on your own or with what you've currently got. A fresh leadership perspective may work to your advantage; if new staff, investments in technology or other elements are needed, capitalize upon a new leader's desire to start out strong and effective. They want to provide you with the best possible tools to get things done and so asking for more resources can also lead to a bigger plate for which you to expand your responsibilities and workload.

For instance, if you're sick of unlocking accounts and performing password resets, reimaging operating systems or performing other menial tasks, suggest an intern who can handle this work and free you up for more meaningful endeavors. Don't forget to cite exactly what endeavors you have in mind to help increase the value you deliver to the organization. You might even calculate how the company can save by paying you X to do more high level tasks and an intern one-fourth of X for the elementary work.

7. Let go of the old boss

As you become acquainted with your new boss and his or her methods, priorities and mannerisms it's important to realize new leaders always take new directions from their predecessors. Don't fall prey to the mindset of "we've always done it this way" or "the last leader told me such-and-such." Any agreements or arrangements made with a prior boss might not necessarily carry over to the new one. Fresh ideas can mean changing course to steer into different directions or entirely new ground.

Resist the urge to compare and contrast your current boss with your previous one, whether in a positive or negative light. Management turnover is common in IT, and being able to remain flexible and work for leaders with different backgrounds, personalities and perspectives will be an important component to your career - and sanity.

8. Understand change is inevitable and roll with it

If you're a stalwart against change, I'd say that IT may not be your field of choice. While certain elements can and probably will remain in place indefinitely - break-fix work, juggling multiple priorities, project deliverables and specific policies or procedures - the platform, tools, and direction involved with your work will always evolve.

Some changes may be for the better, and some may be for the worse. Be ready for the change in either operational practices or technological environment and seek ways to align these with your overall goals - or explain how they may conflict with them. For instance, if a new time tracking system is implemented which takes 30 minutes of your time each day, either use it to demonstrate more staffing is needed because you're putting out too many fires, or explain how it's consuming a half hour that could be better spent focusing on projects or other initiatives.

9. Accept that change won't happen overnight

Be aware that any current problems, pain points or other negative issues you're having will likely need time to straighten out, so don't expect immediate gratification but instead exhibit patience.

For instance, being paged for problems best suited for another department will require your new leader to reassign responsibilities for these tasks through a clear ownership process which will involve new standards, requirements, training, and processes to take the burden off your shoulders. He or she just can't stay "stop paging my employee" since the organization then suffers.

10. Don't be a "yes" person

The purpose of these tips isn't to teach you how to be obsequious or a "yes" person like Waylon Smithers on "The Simpsons," whose job it was to make his boss Mr. Burns always look good. Discuss meaningfully with your new leader any potential issues with their new initiatives or strategy, or else you'll overcommit to endeavors and come off as unrealistic. Provide honest and articulate feedback. Your morale or satisfaction with the company can also be adversely impacted if you take on an "everything is fine" persona which seeks to paper over some difficulties during the leadership transition.

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