Software Selection Cheatsheet (source)
WeMatch.Tech SME edition 2026
Free workbook & cheatsheet

The Software
Selection Cheatsheet

Everything an SME needs to choose the right business software in 48 hours, without a costly misstep. Five steps, three fill-in templates and the figures that matter.

~70%
of implementations miss their goals, usually due to selection and not technology
3 years
the only cost horizon that counts, not the monthly price
48 hours
from first requirement to a well-founded shortlist
Introduction

You choose software once every 7 years. Do it well.

Most organisations choose software on gut feel, on the slickest demo or on the lowest monthly price. The result: a system that doesn't fit the process, that no one uses, and that turns out twice as expensive over three years as expected.

This workbook turns that around. You work through five concrete steps, each with a fill-in part. At the end you have a well-founded shortlist and a vendor scorecard you can defend internally.

5
Questions before every demo
Sharpen your requirement before a salesperson fills it in.
3
Fill-in templates
Cost formula, adoption checklist and weighting matrix.
7
Red flags
Spot a poor match before you sign.
The process at a glance
1
5 questions
2
3-year costs
3
Adoption
4
Red flags
5
48-hour shortlist
wematch.tech · Software Selection Cheatsheet02 / 09
Step 1

The 5 questions before every demo

Answer these five questions before you speak to a salesperson. Walk into a demo without answers and you let the vendor set the requirements.

1
Which problem does this solve, and what does that cost us now?
Put it in euros or hours per month. No number means no business case.
2
Which 3 processes really need to improve?
Three at most. Wanting to improve everything is the fastest route to improving nothing.
3
Who will use this daily?
Involve those people now. Software the leadership picks but the team hates will fail.
4
Which systems must it connect to?
Name them concretely. Integrations are the quiet cost and the biggest blocker.
5
What is our budget over 3 years, including management?
Not the monthly price. The full cost of ownership. Step 2 helps you calculate.
wematch.tech · Software Selection Cheatsheet03 / 09
Step 2

The 3-year cost formula

The monthly price is the tip. Calculate the full cost of ownership (TCO) over 36 months. Here's how that breaks down on average:

100% 3-JAARS TCO
Licence × 36 months35%
Implementation & configuration22%
Connections & integrations13%
Data migration & cleaning12%
Training & internal management18%
Calculate it yourself
Licence × 36 months€  ______________
Implementation & configuration€  ______________
Data migration & cleaning€  ______________
Connections & integrations€  ______________
Training & internal management€  ______________
3-year total (TCO)€  ______________
wematch.tech · Software Selection Cheatsheet04 / 09
Step 3

The adoption checklist

The best software fails if no one uses it. An adoption plan makes the difference between software that lives and software that gathers dust:

Active use after go-live
% of the team
0% 50% 100% Dag 0 30 60 90 dagen
With an adoption plan
Without a plan
Tested by the real users, not just leadership or IT?
An internal owner appointed to drive the project?
A training plan for the first 30 days?
The key workflows set up in advance before go-live?
A measure of usage scheduled after 60 days?
wematch.tech · Software Selection Cheatsheet05 / 09
Step 4

7 red flags in a vendor

One red flag is no disaster. Two or more? Be on guard. Run through this list during and after every demo.

1No references in your sector or of your size
2The demo runs on data that doesn't resemble your situation
3Integrations turn out to be expensive custom work instead of standard
4No clear implementation timeline or go-live date
5The total price only gets concrete very late in the process
6Pressure to sign quickly (“this discount only applies now”)
7No support in your language or outside office hours
wematch.tech · Software Selection Cheatsheet06 / 09
Step 5

The 48-hour shortlist process

A good selection needn't take months. With sharp requirements you reach a well-founded top 3 in two working days.

Day 1Focus & narrow down
09:00
Sharpen requirements
Answer the 5 questions. Record must-haves and nice-to-haves.
13:00
Narrow the market on fit
Gather 6–8 candidates that fit your sector and size.
Day 2Score & decide
09:00
Score 3 to 5 options
Use the weighting matrix on the next page. Be strict on process fit.
14:00
Shortlist with reasoning
Choose the top 3 on score, not on gut feel.
16:00
Schedule demos, only with the top 3
Only now speak to salespeople. Armed with requirements and a scorecard.
wematch.tech · Software Selection Cheatsheet07 / 09
Bonus template

The vendor scorecard

Score each option 1–5 per criterion, multiply by the weighting and add up. The highest weighted score wins. Objective and defensible.

Criterion Weighting Score 1–5 Weighted
Process fit: matches your way of working25%______
Ease of use & adoption20%______
3-year costs (TCO)20%______
Integrations with your systems15%______
Vendor & support12%______
Implementation time8%______
Total100%___
Tip
Fill in this table separately for each option on your shortlist. Then compare only the total scores. That stops one impressive demo from colouring your whole decision.
wematch.tech · Software Selection Cheatsheet08 / 09
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© 2026 WeMatch.Tech · Independent software advice for SMEs09 / 09