The 10 rules of courtship before saying “I do” to software

By: Matt Stocker

It might sound somewhat geeky but I love software! By software I mean the programmes that sit on our computers, mobile devices and in the cloud that have been designed to make our devices useful and our lives easier. We live in an age in which there is unprecedented access to high quality software, both at home and in business. Software is a growing, thriving market, with low barriers to entry, and the fact that investors are willing to back software is only increasing the availability of great solutions.

For me, I love comparing and choosing software, using it, getting to know it and learning about the efforts and ideas that developers have put into their baby. I love the power that software has to transform an action, a process or even an entire organisation.

The trouble is that choosing and using software can be a bit of a Marmite process—especially in a business environment. You’ll either love it or hate it. Software inevitably transforms your life one way or another—for good or for bad! Generally, the more core a software solution is to key business processes, the more this is true. Choose and commit to the wrong software solution and you can bring a business to its knees very quickly. I’ve seen this happen a number of times to unsuspecting organisations and it’s not pretty!

Think of selecting software as a little like marriage—it’s easy to commit but hard to get out of. When you achieve the perfect match, life couldn’t be better. But get it wrong and separation tends to be a painful, messy process.

So what are the rules of software commitment that minimise the risk of marrying in haste and repenting at leisure?

1. Understand yourself and what you are looking for

If you don’t understand yourself, your organisation, and how you work, you won’t be able to decide what you’re really looking for and whether there is a good fit or not. Most people have some sort of list for ‘My ideal partner is…’, based on their own understanding of themselves and what they feel would work in a relationship. Choosing software is not much different. Although ideal partner lists aren’t always 100% correct and you may later discover that certain assumptions were wrong, developing an ideal software list is a great start to the selection process. Before you begin to select any software, it’s vital that you first understand your business, the core processes that make your business tick, and what success looks like for you. What features can you really not live without? What are you happy to compromise on? What are the end objectives that you want to achieve? These are the criteria that will help you to find your ideal partner.

2. Work through stuff together

Looks aren’t everything, right? While aesthetics are obviously important in the attraction process, there is a strong case for the ‘It’s what’s inside that counts’ perspective to gauge how well you will get on as a couple over the long term. And the only way to really find out what’s inside is to work through important stuff together. You need to find out whether your individual approaches to life are remotely on the same page. Committing to software is much the same. It’s vital to work through real business scenarios with the software yourself and you should always insist on both a demo and trial that uses your own case studies, data, processes and tasks. Don’t just rely on standard demos and don’t let a salesperson do it all for you—they are practiced at making their software look brilliant and easy to use, even when it’s not! By working through practical scenarios and day-to-day processes, you’ll soon begin to see whether you have an attraction that goes beyond the first few clicks!

3. Dig deeper

With software, as with people, sometimes not everything is as it appears on the surface. That’s to be expected—we don’t always like sharing our weaknesses, especially when they make us vulnerable. A software sales person is even less likely to be completely open and honest with you as it’s in their best interests to make a sale. The website of a software product is also unlikely to list everything that the software can’t do. That’s why it’s up to you to ask the right questions and dig deep. Software sales can be a case of ‘truth by omission’ so it’s your responsibility to find out what they haven’t told you. Unfortunately, this courtship tends to be a bit more one-sided than is ideal but, with software selection, I’m afraid that’s the way it tends to be. Caveat emptor—let the buyer beware!

4. There is no such thing as the perfect partner

As Debbie may occasionally tell you on a bad day, there is no such thing as the perfect husband—I know, shocking right?! And likewise, there is no such thing as the perfect software. Unless you buy a bespoke solution, no software will have been designed for you personally but rather for someone a bit like you. This means that it’s highly unlikely you’ll find software with a perfect fit. You therefore need to look for best fit solutions—software that most appropriately fits your processes and that you can live with on a daily basis. Of course, each solution will have its own strengths and weaknesses but inevitably you’ll be able to live with some, whilst others are going to drive you insane! The secret is choosing the former and avoiding the latter.

5. Know where to draw the lines

Different relationships work in different ways—it may be that you’re responsible for the admin and your partner looks after the garden. Maybe you co-parent your kids. Wherever the responsibilities lie in a relationship, it’s always an idea to play to your strengths. If both of you suck at housework or DIY, you might hire a cleaner or a handyman. Knowing where to draw the lines between software works in a similar fashion. It isn’t often that one piece of software can be all things to all people. Indeed, software that claims to do everything is, in reality, often unwieldy and mediocre at most things, whilst being excellent at few. You will therefore need to decide which software solutions will best look after which processes. You’ll also need to consider how the solutions will effectively integrate with one another without things dropping through the cracks. Making these decisions often requires a bit of juggling as you work out what fits where and the boundaries will, on occasion, require reworking and renegotiation. But, as with any successful relationship, that’s all part of the fun!

6. Don’t think you can change them

Starting any relationship with the aim of changing your partner into something they are not is a dangerous plan and one that’s doomed to failure. The fact is, people don’t change easily. Evolve? Yes. Change? No. Established software is similar in its inability to accommodate significant changes. The sales people or developers may promise change but in reality it’s not that simple. Software tends to be built around a fundamental concept, philosophy and envisaged use scenario, so promising change is the equivalent of an architect promising to create a mansion out of a bungalow. Yes, it’s technically possible but only if you knock it down and start again. In most cases, you might as well have bought a mansion in the first place! As a rule of thumb, tweaks are fine but you should be very sceptical of promises for deep changes to core functionality. Such changes are usually risky, expensive, create more problems than they solve, and are often no more effective than putting lipstick on a pig! Software as a service (SAAS) solutions tend to be even more inflexible. By its very nature, SAAS offers a one size fits all solution—the entire business model hinges on solutions for the masses. Whether software as a service or boxed software, whatever you do, don’t commit to it based on a vague promise of added functionality sometime in the future.

7. Ask the children

I’m not for one moment suggesting that your staff are your children or that you should treat them as such! However, much like parental decisions not only affect the adults but also influence the children, you need to realise that a software partnership isn’t just between you and the software provider—others within your organisation are going to have to live with your decision day in, day out. Get your colleagues involved at an early stage. Involve them in developing the statement of requirements, invite them to meetings, and ask them to test the software themselves. Be conscious of those people who will be most impacted by your decision—they will usually be the ones who get shouted at if they can’t do their job properly due to poor software and they won’t thank you for a poor choice! Where possible, make a business-wide decision as to which solution to commit to. Remember, unlike children, your colleagues can walk out if you get it really wrong. Businesses have lost good staff through poor software selection and implementation because dealing with bad software on a daily basis made their jobs nigh impossible.

8. It’s not just about the wedding

Long-term marital success is as much about life after the wedding as it is about your partner selection and promises of commitment. You need to give each other time to settle in and adjust. Make time for one another, continue to talk, resolve differences, and put one another first. In a successful software partnership, continued commitment following the initial selection process is vital. Surprisingly, choosing your software is actually the easy bit of the process. Without a full and proper implementation, you could in fact create a failed project even if you have selected the right partner. In rolling out the software you should be aware that staff will need training; an effective transition from the old way of working to the new will need to be made; and there are likely to be teething issues that will need to be resolved. Longer term, adjustments will need to be made to ensure that the software continues to evolve with you. Of course, you can’t do this on your own. Both you and the software provider need to remain completely committed for the long haul, even—or should I say, especially?!—after the initial honeymoon period is over.

9. Trust is important

Trust is important for any relationship and especially for one in which there is a long-term commitment. Without trust, a relationship can be at best difficult and at worst impossible. Likewise with software, the concept of trust is critical. You need to trust the software’s security, its resilience, your backup of the data, the service level agreement (SLA), and the fact that the future road map of the software is going where you need it to. After all, you are entrusting your business to this software. Not only that but you need to remember that you are not just choosing the software itself but also the people and the organisation behind it. You will be reliant upon the competence of the team who develop and build it; the responsiveness and helpfulness of those people who answer your urgent support requests; and the wisdom of the owners and managers who determine the long-term direction and success of the business. Can you trust them to do good by your organisation? Do they really understand your needs? Are they consistent and congruent in their relationships? Are they people you’ll enjoy working with well into the future? By doing your due diligence upfront, you’ll reduce the risk of being disappointed and heartbroken later on.

10. Money matters

Research suggests that money is one of the topics most argued over in a committed relationship. Differing expectations and differing priorities have to be worked through, compromises made, and a shared understanding developed if money isn’t going to become an issue that gets in the way of a relationship. If this kind of understanding can’t be reached it begins to suggest the partners might indeed be incompatible. Likewise with a software partnership, financial priorities and budgeting can be an issue. Knowing how much to spend on software is not always obvious, especially when price is not directly correlated to quality or even value. In reality, you can only ever really make a comparative decision between differing software options, balancing the complex mix of functionality, best fit, price, licensing model, consultancy and training fees, ease of implementation and upgradability. In the end, you’ll need to choose the solution that you feel provides the best return on investment. It may be that you have a natural tendency to spend very little or to spend a lot. At the end of the day, it’s not about your personal spending preferences but about the business case, the range of software options available to you and, ultimately, what will be best for your business—even if it takes you out of your comfort zone.

Enjoy the process

Hopefully I haven’t scared you off either marriage or software selection after all that! As I said at the beginning, I love software and, as Debbie will testify, I get particularly absorbed during a software selection project largely due to the fact that I’m having so much fun! I’m also an advocate of healthy and happy marriages—after all, I found not only my wife but also my business partner too.

Whilst some businesses are happy to approach software selection with little more thought than a drunken and impromptu wedding to a stranger in Vagas, only to wake up the next day regretting the fact that they didn’t put a bit more thought into choosing a more suitable partner, there are some who are wiser and heed the call to approach software selection as you would a serious courtship. Hopefully, you, dear reader, fall into the latter category!

Also, do remember that, much like marriage, you need to go into software selection knowing that you’ll always have a lot to learn. So be willing and able to get stuck in. Grow. Make mistakes. And, most of all, enjoy the process! Sometimes, even if you follow all the rules and do absolutely everything right, it won’t always work out, but at least you’ll be able to look yourself in the mirror and say, “I gave it my best shot.” And, after that, you will pick yourself up and start over again.

Article by:

Matt Stocker

Matt is founder and director of Stocker Partnership, a strategy and innovation consultancy. As a strategist, designer, innovator and geek, he's known for his creative thinking. Matt thrives in challenging environments and loves to push the boundaries of possibility. He's a big picture, visual thinker who is always running 5 to 10 years ahead. Find out more

Related Articles