Let's begin with some potentially hard truths. The majority of technology problems are not unique, they've been solved before and there are many solutions for them. Therefore, your primary question should be "Do I really understand what my problems are?"
Great news! You've decided to implement some new technology or to upgrade your existing technology stack. Maybe you want to increase performance, maybe you want to automate particular business processes, or maybe you're ready to make the jump to the cloud for your business. So much to think about, so little time to get it done. For these reasons, you've decided to bring in some outside help. That's a great move and a great start, but without raining on your parade, there are a few pitfalls you need to avoid.
Firstly, when you need help with something outside of your comfort zone or skill set, the wise move is to bring in a third party who is the perceived expert in that area. Software providers and development agencies are businesses too and as such, have put their own stakes in the ground with regard to what products they sell (e.g Wordpress agencies) and how they will want to build your solution so that it fits into their operational boundaries in terms of support and up-selling and things of that nature. This needs to be taken into account before you engage. Industries like Banking and Insurance get caught by this all the time. Because they are so huge as organisations, with very deep pockets, they believe that money solves all and end up paying over the odds for third party, off the shelf software products that are then adapted to fit their systems. Think the square peg in a round hole scenario. This can only go so far and is not the platform from which to build your technology stack as a small business. You need things to fit your requirements, like a glove and to provide a solid base from with which to grow, without the need for expensive rework in the future.
Secondly, there are two types of people or organisations in the world from a software perspective. Those that understand the true cost of software and technology and those that don't. And this cost is not just a financial cost, but an organisational and operational cost also. It's perfectly fine to be the latter, you do not need to be an expert in the technology field to deploy a great technology stack for your organisation, you just need to be an expert in knowing exactly what your requirements for software and technology are. As for the former in the above equation, they have the responsibility to educate and inform their clients as well as sell them solutions. Any software and technology provider that empowers their clients over time are valuable. Those that keep you in the dark and uneducated about your technology situation or possible options, whether in their skill set or not, are only going to be detrimental to your organisations software and technology health. Therefore, if both sides of this coin are balanced then we have quality software being produced and happy and empowered clients everywhere. It is perfectly achievable.
Thirdly, and most importantly is knowing what you are doing before you engage a software provider. This doesn't mean that you need to know exactly what type of technology you need or anything that detailed. That is the remit of the third party software and technology provider. No, you just need to know your organisation, your people, their roles and what you want to achieve. This is not some fluffy feeling type of knowing, this has to be as detailed as you can make it. It is this detail that any decent software and technology provider will dive into to develop your software and technology solution. You want to reduce this type of engagement to a minimum as it is in this phase of a project that the majority of up selling occurs. Fear, uncertainty and doubt are thrown in to make you think either your problems are bigger than they actually are, or that the software solution you have in mind, is smaller in scope that it needs to be. The cost of a software and technology solution can skyrocket here and decisions made at this stage can have financial and technical ramifications far into the future. Be wise, organise and discuss what you think you need with all relevant departments in a candid and open manner and have the compassion and empathy to listen to the various concerns that the end users might have.
Ok, so you've understood that you need to have the power during any engagements with third party software and technology providers. What does this look like in reality and how do you go about pulling it all together before any engagement begins. It might look something like this
Does every stakeholder in your organisations decision to upgrade or deploy new software and technology truly understand what technology you have deployed at the present time? If not then this is your first step. It is a fallacy to think that you can decide with any authority on a solution if you do not know what it will be replacing. Talk to the relevant people, let them educate you on what is in operation now and most importantly of all, listen and take note of the real life problems with your existing software and technology or indeed your business processes that need automation. This is your "What And Why"
Once you know what you have, you then discover what you need to have in the future. This type of discovery is not just a C-Suite or Executive Level exercise. This is not performed by those that will be ultimately paying for the solution. The golden information uncovered during this phase will come from the users, your employees and ultimate users of the solution. Ego and hierarchy must be put aside so that everyone at the table can feel like they can be as open as possible. You will then uncover the truth about what you truly need, what is nice to have and also, most importantly, what is overkill for your day to day operations. This phase should also take note of how many users you will have, are they grouped in any way according to skills, seniority, auditing and compliance or any other organisational boundaries you may have. User management is one the core functional pieces of any serious software and technology platform. Know this in advance of third party software and technology provider engagement. This will be your "Wish List"
With your "What and Why" and your "Wish List" you are now ready to engage with third parties. Your meetings might look something like this. The third party will arrive to the meeting and begin to engage you in a discovery phase to assess what you have and what you need. Here you can take control of the conversation and begin with a confident position and state "We have technologies x,y and z at the moment serving our N number of users over N number of groups in the organisation. We have performance issues and efficiency problems in processing our work and are looking for technologies that will allow us to work more efficiently and at a reduced cost. We are interested (not interested) in Cloud Solutions and we expect to grow our users by 20% in the next 2-3 years"
What you've done here is this shown that:
All this information serves two purposes. One is to answer a lot of questions that the provider would most likely have to discover during the engagement. Any good provider will love this, as it is always good to work with an organisation that knows what it wants and what it expects from the engagement. Possibly more importantly, it has shown the third party software and technology provider that you are technology and software aware and they will have limited scope to up sell or use FUD to inflate your solution beyond what your immediate requirements are. In short, yur first meeting should be much more informative, efficient and you should be able to give a hard yes/no on whether the provider is right for you at that stage. This saves everyone time and money as potential clients can loop over many providers to find the right fit in a short period of time and providers will know where they stand very early on and reduce their lead generation efforts.
If you have followed all the above, you will find that your process of engagement was easier, your requirements were understood well in advance and the scope for error will be reduced overall. This means that the provider can work better as they are fully informed, your organisation gets exactly what they needed and wanted with you technology and software project and everyone wins. Obviously this is the real world and there will always be mitigating circumstances that might interfere with the perfect project, but being prepared and fully informed was never a point of failure for any project.
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