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We have hired someone to be the new boss of my department (the old boss left). I was one of the interviewers for the new boss, and along with other technical peers did some of the boss' tasks while we were without a boss. But my (and my peers) jobs are very tactical. We organize the herd of cats that are software engineers, and our boss is meant to be the more strategic sort of figure that helps our department work with others.

I am in an awkward spot because my boss' boss(es) have very little insight into the day to day operations. I'm wondering if there are any well known best practices for someone in my position to help onboard my new boss - how to set them up for success in the new role?

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    I'd start by recommmending you don't use adjectives (like onboard) as verbs, nor would I refer to your subordinates as a "herd of cats". – user9158 Dec 11 '13 at 3:00
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    @LegoStormtroopr - Sorry, around here onboarding is used as a verb to describe getting someone "on board" with things - up to speed. Is there a more correct, similarly terse term to use that would improve the question? – Telastyn Dec 11 '13 at 3:27
  • "educate" and "bring up to speed" spring to mind. But I've started a question on English Language and Usage that may prove fruitful. – user9158 Dec 11 '13 at 3:41
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    @Telastyn As a non-native English speaker I had to guess at the meaning of your 'verb'. It's not hard to guess, but it interrupted my reading flow. If you want as much input as possible, don't introduce hurdles like this (Other hurdless are e.g. a 'wall of text' or writing 'u' instead of 'you'). Please edit your question. – Jan Doggen Dec 11 '13 at 11:09
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Looking at the role that you play and your boss will play, he would find someone very useful who can help understand & project (externally) the team's tactics/operations and align them with the company's strategy (as your boss's bosses understand it).

I would pair with him and hold workshops/q & a sessions to educate/demonstrate -

  1. Why is the team doing what it is doing ?

  2. How is the team doing it ?

  3. How are 1 & 2 connected and in sync ?

  4. How would they be tracked and remain in sync ?

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Less interruption from your side will give your boss more time to concentrate on his job. Know how to communicate in emergencies. Know what kind of information help your boss best make a decision and try to provide them in right time.

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Three things that will help:

  1. Collectively, your team should help him structure the project schedule so that he has a realistic idea of at least current completion estimates. If you see 'bumps in the road' - issues that might derail the schedule or the project, bring these up right away.

  2. If users are attempting to guide the delivery priorities you should name those users to the boss, so that he can go talk to them. Now that he's there all requests should be directed to him.

  3. There may be some value in discussing the workload balance, to see if someone is carrying more or less weight than they should, and recommend a rebalancing if need be to redistribute the load. I recall a situation in particular where I was getting paid more then someone I viewed as an equal co-worker - this was in a startup situation where cash was precious and the two of us were friends of about five years. I suggested after a few weeks that the pay between us be equalized.

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