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I am relatively new to my current job, but I have a lot of ideas of how to improve the current working environment in terms of productivity, software quality and performance. I aim to be having a meeting with the bosses of this small company, in which I hope to convince them to invest in some new, professional software that would make development a lot easier.

My question is: how do I approach this meeting so that I can convey the best benefits of the software without seeming to be demanding anything?

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Essentially your asking them to spend more money. What they may hear is more expenses. What you want them to hear is low risk investment opportunity. These may sound like the same thing (and they are) but stating things in the later form will usually be more successful.

Put yourself in the shoes of your manager and ask & answer questions from their perspective. Specifically, focus on things that answer the question... "What is the return on investment?"

Articulate what you predict will be the return on their investment.

  • I (or we) will be able to be more productive and will be more likely to deliver on schedule (possibly sooner)
  • I (or we) will have lower defect rates
  • I (or we) will have greater capacity for XYZ
  • X automation will lead to reduced expenses in Y area over Z period
  • Etc...

Good luck.

  • +1, and quantitative estimates will be needed for those "lower-sooner-greater" stuff. – sharptooth Dec 20 '11 at 13:58
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You cannot sell anything without an established problem, want, or need. The SW is a solution; benefits of it does not necessarily mean the organization has a problem, want, or need. JoeGeeky outlined how to present the business case for your SW solution; however, you have a step before this. You need to build a case to build a case for the solution.

In other words, you need to get buy-in that there is a problem, the first step in any sales call. And you need to show how this problem is affecting their goals as it rolls up, e.g., affecting adversely revenue and profit. And you should approach this solution agnostic.

  • SW is not always a solution, many pieces of software are a problem by themselves - and good managers know that. – sharptooth Dec 20 '11 at 13:59
  • Not in the context of the OP's question. Our answers cannot cover every single possible scenario and the SW piece was not really the compelling part of my supposition. – David Espina Dec 20 '11 at 16:23
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Once you have a reputation of success, it will be much easier to ask them to spend money. Build a track record of solving problems that doesn't require them to spend more money.

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The first thing to identify are the current "pain points" of the bosses. For example did they not get a bonus last year because a software project was late? Did they have to come in and work a holiday weekend because of a system problem? In other words, if they have no problems, why should they change? Remember that in general people are change adverse. Change is generally associated with uncertainty and at least some pain.

Next consider how your proposal(s) will address those pain points, what is in it for the bosses?

Finally remember that this is not simply a money problem, it is a multi-dimensional change. At a former employer we spoke of the hexagon of change; the 6 areas which must be addressed in any plan. Namely:

  • Business Process – Organization – Location – Application – Data – Technology

So for example the Organization domain would address any training which would be required as well as changes to job descriptions or team re-structuring.

Anyway cross all the Ts and dot all the Is before the meeting and you have a much greater chance of success.

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All answers provides very good insights, but I noticed most of them are attached to the idea that investing means buy... so, two things that could be clarified:

  • when you mean invest, you'd like to suggest to the owners of this new small company you're working on to buy new productivity softwares or you mean investing man-hours developing new softwares?

  • Have you searched for free similar softwares?

My point is: there's a slightly possibility of having your bosses hearing your suggestion not as more expenses, but as something that could add value into your daily work.

I see you're a person that's called a 'prophet', a people who thinks beyond the ordinary things. However, there are barriers to cross from a prophet to become a builder... and the first one is to prove that what you're thinking really applies to the scenario you have in place.

I'd go for something like this:

  • Brainstorming the idea with some teammates (or maybe part of the idea, in case you're afraid any of them could 'steal' your ideas) and pick some that buy it in;
  • Once you have some people, startup a pilot, probably applying a free version of the softwares you want to suggest to your bosses;
  • After a while, you'll have the first experiences and outcomes of your suggestion... and will have something to be based on when getting back to your bosses beyond 'I have an Idea'. At this stage, you'll have an idea and some proofs that your idea really works.

And, only after you're comfortable your ideas really worth, I'd go for the meeting with the bosses.

Hope it helps!

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