Questions to ask any PPM software vendor and why the right ones depend on who's asking

What to expect in this vendor-neutral guide

Match questions to roles

Get answers that actually matter

Don’t trust rankings alone

Verify fit with your own questions

Uncover true costs early

Avoid budget surprises after signing

Post go-live value matters

Support and flexibility protect your investment

Guide provided by: Bubble PPM Software

A globally-operating leader in the field of

PPM Software

Founded in 1999, our company builds software that helps organizations master modern work management.

Our cloud-based solutions provide instant visibility into your entire portfolio, with the intelligence and tools your teams need to deliver on time, on budget, and on strategy.

Questions to ask a PPM software vendor and why the right ones depend on who’s asking

A vendor-neutral guide from the team at Bubble PPM

Author disclosure:

Most of what follows has nothing to do with which PPM software platform you eventually choose – it’s about making sure the right people in your organization are asking the right questions before a vendor is selected.

Estimated read time: 7 minutes

Introduction

Investing in project and portfolio management (PPM) software is rarely a decision one person makes alone. Ask a PMO Director, a Finance Director and a project manager what “good” looks like from the same platform, and you’ll get three different answers. The Finance Director wants a defensible three-year investment cost. The PMO Director wants governance and audit-readiness. The project manager just wants his or her Friday afternoon back from status-chasing.

Most PPM buying guides flatten all questions into one generic list “20 questions to ask a PPM software vendor before you buy their software”, as if a Chief Operating Officer and a project coordinator should walk into the same vendor call with the same script. In practice, the questions that actually expose whether a platform will work are different depending on who’s asking and what they stand to lose if it doesn’t.

This guide splits them accordingly, into questions for that senior leaders should ask and questions that project managers and their teams should consider.

If we’ve missed anything, or you think there’s better questions that can be asked email us HERE

Why you shouldn’t stop at analyst reports and vendor grids

It’s tempting to let a Gartner or Forrester report – or a G2 grid – do the shortlisting for you. They’re useful starting points, but treating them as the answer rather than an input causes two specific problems worth knowing about before you rely on them.

First, analyst quadrants score vendors against criteria the analyst firm sets, and those criteria tend to reward breadth: global support footprint, size of professional services organisation, depth of adjacent modules. That’s a reasonable proxy for “which vendor is safest for a 50,000-employee multinational,” but it says very little about fit for a mid-market PMO running a specific delivery methodology in a specific sector. A vendor can sit outside a “Leaders” quadrant simply because it chose not to compete for enterprise-scale accounts, not because its product is weaker for your use case.

Second, review-site grids like G2’s are built substantially from review volume and market presence, alongside satisfaction scores. Market presence correlates strongly with marketing budget and company size – a vendor with ten times the sales headcount will generally collect reviews faster than a smaller, more specialised one, regardless of how happy either set of customers actually is. A “top right” position tells you a vendor is well known and reasonably well liked. It doesn’t tell you whether it’s configurable enough to match how your organisation actually runs a gate review, or whether its pricing works for your headcount.

The practical takeaway: use analyst reports and review grids to build a longlist and sanity-check that a vendor is a stable, going concern – then set them aside and run your own evaluation using questions specific to your organisation. That’s what the rest of this guide is for.

One scoping note before we get into it: this guide deliberately stays broad and platform-agnostic. A handful of meatier, more specialised topics deserve their own dedicated treatment rather than a rushed paragraph here, so you won’t find them below – this is about the questions that hold up regardless of your sector, delivery methodology or deployment size.

The same software, two very different conversations

Before the question lists, it’s worth being explicit about why the split matters. The two groups aren’t just asking about different features,  they’re protecting against different failure modes.

Table 1: The different mindset and concerns of each group

Keep that table in mind as you read the two sections below and, ideally, bring both groups into the room during vendor evaluation rather than letting one answer on behalf of the other.

Questions to ask a PPM software vendor - if you're a leader

Part 1

Senior leadership questions to ask a PPM software vendor

Leadership stakeholders – PMO Directors, COOs, Finance Directors, portfolio sponsors – are typically the ones signing off budget and answering for the decision at board level a year later.

Senior leadership stakeholder questions should test two things above all: whether the platform will genuinely improve the quality of investment decisions, and whether the true cost and commitment are visible up front rather than discovered in year two.

If you’re approaching a vendor from this point of view, perhaps resist the immediate pull of a polished, feature-rich demo at this stage and ask some direct questions. The questions below are designed to surface answers to the concerns outlined in table 1 (above).

Table 2: Questions Senior Leaders should consider asking

Question to ask Why it matters What a credible answer sounds like Watch out for

Total cost of ownership deserves one more level of detail, because it’s the single area where leadership teams most often get surprised after signing. Push for a specific answer on each of these lines before you commit:

Table 3: Leaders should also consider total cost of ownership

Questions to ask a PPM software vendor - if you're the PM or on the Team

Part 2

Project Manager & Team questions to ask a PPM software vendor

Project managers and team stakeholders – your Subject Matter Experts (SMEs), your Finance team, your Analysts, Marketers, Engineers and 3rd party collaborators – typically create the core system value. Their inputs and impressions matter and ultimately it’s their adoption that determines whether the investment actually pays off.

If leadership is buying a decision-making tool, project managers and teams are buying a piece of their working week back (or they’re not). As a group, you’ll live inside the platform daily, so your questions should focus on friction: “does this make my job easier”?, or “does it just add a new system to update alongside the old habits that never quite went away”?

While you may be the key influencers during the initial vendor scoping and selection phase, it’s also worth remembering that PMs are rarely in the room for the commercial negotiation. Getting your questions answered and being actively involved in any demos and discussions, not just leadership, is one of the more reliable predictors of whether a PPM platform rollout sticks.

Table 4: Questions Project Managers & Teams should consider asking

Question to ask Why it matters What a credible answer sounds like Watch out for

Where Bubble PPM fits into this

We’d rather you use the questions above with any vendor than skip straight to a sales pitch – that’s genuinely the point of writing this. However, since we’re the ones publishing the advice, it’s fair to point you towards a few of our own resources.

If you’re a member of the leadership team:

More information is available in either of these third-party reviews of Bubble PPM. Note: Links to 3rd party websites open in new window.

  • G2.com HERE
  • Work-Management.org HERE
  • Digital Project Manager HERE

You can also read more on our page for senior leaders.

If you’re a member of the project delivery team:

You can also read more on our dedicated page for project managers.

Conclusion

If the questions above feel like the right ones for your organisation, the most useful next step is simply to ask them – to us – or of anyone else on your shortlist. If you’d like to put them to us directly, you can submit a question or request a demo. Bring either or both your leadership team and your project managers to the conversation and we’ll go from there.

If you’ve had a look around our site and feel that Bubble PPM isn’t for you then accept our best wishes for the rest of your search.

As a final word – Remember, selecting a PPM solution partner is ALL about identifying the provider that fits your unique needs best. The road to finding that fit should be a journey and not a race.

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