Author: Niranjalee Rajaratne

There is a version of this article that lists every AI product that launched this year and gives each one a star rating. This is not that article.

What follows is the shortlist — the tools that are open on my screen on a regular working week, what I actually use them for, and where they fall short. No hype. No affiliate links I can’t stand behind.

The honest context first

I work across programme delivery, PMO governance and technology strategy. My use cases are: structuring complex thinking quickly, processing meeting outputs, drafting stakeholder communications, and researching topics I need to get up to speed on fast. Your mileage will vary based on your role.

ChatGPT Plus

Still my primary thinking tool. I use the GPT-4o model for: structuring reports and governance papers, rewriting dense prose into plain English for executives, sense-checking project risk registers, and generating options when I’m stuck. The o1 reasoning model is genuinely useful for complex dependency analysis — it thinks before it answers.

What it isn’t: a replacement for domain knowledge. You still need to know what good looks like to evaluate what it gives you.

Notion AI

I moved my knowledge base to Notion about two years ago. The AI layer added on top has changed how I use it. Most useful feature: “ask your workspace” — querying notes, documents and meeting records with natural language. For anyone managing a complex portfolio, having a searchable, AI-queryable knowledge base is genuinely transformative.

Otter.ai

I use this for meeting transcription. It connects to Google Meet and Zoom, transcribes in real time, and produces a summary after the call. The summary quality is uneven, but the searchable transcript is the real value — being able to search “what did we decide about the budget approval” three weeks after a meeting is worth the subscription alone.

Perplexity

My replacement for Google for most research tasks. It synthesises sources and gives you a cited answer instead of ten blue links. I use it for: understanding regulatory changes quickly, researching vendors before procurement decisions, and getting up to speed on a new technical domain. The Pro version adds more sources and better models.

What I don’t use (and why)

I have tried: Copilot (too shallow for complex tasks), Gemini (improving, but not there yet for my use cases), Claude for everything (strong at writing and reasoning, but I don’t reach for it as my daily driver — yet). This will change. This space moves fast.

The honest summary

AI tools don’t make you better at your job. They make you faster at the parts you’re already good at — and they expose the parts where you’re unclear in your thinking. If you give a vague brief to an AI, you get a vague output. The discipline of being specific is the actual skill.

Start with one tool. Use it properly for a month before adding another.

I have been involved in transformation programmes for most of my career. I have seen some work. I have seen more fail. The ratio is not flattering.

The post-mortems on failed transformations tend to blame the same things: lack of executive sponsorship, poor change management, technology that didn’t deliver. These are true, as far as they go. But they’re symptoms. The root causes are less comfortable.

The transformation is the strategy, not a programme of it

Most organisations treat transformation as a discrete programme with a start and end date. The technology gets delivered. The “change” gets managed. The programme closes. Six months later, people are using the old spreadsheets again.

The organisations where transformation actually takes hold treat it as a continuous operating model shift — not a project to be delivered and signed off. The difference in framing changes everything: governance, resourcing, measurement, and what success looks like.

The business case is written to get approval, not to guide delivery

I have reviewed hundreds of business cases. Almost all of them are written to get investment approved. The benefits are optimistic. The risks are understated. The delivery assumptions are best case.

Then the programme starts and the real world arrives. But the governance framework is still tied to that original business case — so you spend the next two years managing against projections that were never realistic, explaining variances rather than making decisions.

Good transformation governance separates the investment case from the delivery framework early. The case gets you started. The delivery framework has to evolve with what you learn.

The people who know where the bodies are buried aren’t in the room

Every organisation has people who know how things actually work — which processes are workarounds, which dependencies aren’t documented, which teams will resist and why. They’re usually not the people in the transformation steering group.

The organisations that avoid the worst delivery surprises invest heavily in operational discovery before they start designing solutions. Not a two-week current-state assessment. A genuine, sustained effort to understand how work actually gets done, by the people who do it.

Change management is an afterthought, always

I know this because I have said “we need to bring in change management resource” at roughly the midpoint of every programme I have ever worked on. By then, the design decisions are made. The technology choices are locked. The change manager is handed a solution and asked to make people want it.

This doesn’t work. Change capability needs to be in the room when you’re deciding what you’re building and why — not when you’re trying to land it.

The few things that actually work

A clear problem statement that people believe in. Not a transformation vision. A specific, honest articulation of the problem you’re solving and why it matters.

Governance that makes decisions, not reports on status. A steering group that meets to resolve issues and make calls — not to receive RAG updates.

A delivery team with real authority. Programme managers who can say no, change scope, and escalate effectively. Not coordinators.

Measurement of outcomes, not outputs. Not “we delivered the system.” What changed because of it?

And the thing nobody wants to hear: time. Real organisational change takes longer than any business case will tell you. Build that into your expectations from the start.

I am going to tell you upfront that this article is about Monday.com. I want to get that out of the way because there are a lot of “best project management tools” lists on the internet, and most of them are nonsense written by people who have never run a portfolio.

I have run a portfolio. I have tried a lot of tools. Monday.com is the one I’ve kept coming back to, and I’ll tell you exactly why — and where it falls short.

The problem with most portfolio management tools

Most tools are built for single-project tracking. Even the ones that claim portfolio capability are, in practice, a collection of projects with a rolled-up view bolted on. The result is that programme managers spend their time aggregating data from multiple sources, building reports in spreadsheets, and fighting their tooling to give them the view they need.

The tool should give you the view. That’s the job.

What Monday.com does differently

The core of Monday.com is its flexibility. Unlike Jira (which pushes you into a specific agile methodology) or MS Project (which is built around a Gantt and fights you if you want anything else), Monday gives you a board structure you can shape to your governance model.

For portfolio management, I use it like this:

A portfolio-level board with one row per programme, showing RAG status, phase, delivery lead, key milestones, and financial tracking. This is my steering group view — everything I need for a governance conversation in one place, without opening five other things.

Programme-level boards underneath, each with their own workstreams, dependencies, risk registers, and action logs. These feed upward to the portfolio view through dashboard widgets.

A risk and issues register as a separate board, linked to programmes, with ownership, status, and escalation path tracked per item.

The automation features are underrated. I have automations that alert me when a milestone status changes to red, when an action is overdue, or when a risk rating increases. It removes the manual chasing that consumes so much of a programme manager’s week.

Where it falls short

Resource management is weak compared to dedicated tools like Resource Guru or Smartsheet. If resource capacity planning is central to your governance model, you’ll hit limits quickly.

The financial tracking is basic. I track budget vs actuals in Monday but I do the detailed financial modelling elsewhere — it’s not a replacement for a proper finance system.

It’s also not cheap at enterprise scale. The pricing works for small teams; at programme level with multiple users, costs add up.

Who it’s for

If you’re managing a portfolio of work, need a flexible governance framework, and are tired of spending Monday mornings building status reports from five different sources — Monday.com is worth evaluating seriously.

They offer a free trial. I’d recommend taking it with a real piece of work rather than a test scenario. That’s the only honest way to evaluate a tool.

Radical Candour has become one of those terms that people deploy without doing the reading. I have sat in leadership development sessions where it was used to mean “I’m going to be blunt with you now.” That is not what it means.

Kim Scott’s framework is more precise and more demanding than most people who cite it seem to realise. Understanding it properly changed how I manage — and how I receive feedback.

What it actually is

The framework has two axes. One is whether you challenge directly. The other is whether you care personally.

Radical Candour sits in the quadrant where both are true: you care enough about someone to tell them something difficult, and you’re direct enough to actually say it rather than hint at it.

The three failure modes are:

Obnoxious Aggression — high challenge, low care. Being blunt without the relationship or the genuine concern to back it up. This is what people often mistake for Radical Candour. It isn’t. It’s just aggression with a framework attached.

Ruinous Empathy — high care, low challenge. Caring so much about how someone feels that you don’t tell them the thing they need to hear. This is the most common failure mode among well-intentioned managers. You let someone walk into a performance review unaware of a pattern you’ve been watching for six months, because you didn’t want to have the difficult conversation. That’s not kindness. That’s a failure of care, disguised as it.

Manipulative Insincerity — low on both axes. Saying what you think someone wants to hear. Giving vague feedback that doesn’t actually land anywhere. Most performance management conversations in most organisations.

What it looks like in practice

The hardest part is the timing. Radical Candour is most useful when it’s immediate. Feedback given three months after the fact is not feedback — it’s a history lesson.

I have had to learn to say the thing in the room. When a senior stakeholder presents a plan that has a significant gap in it, saying “this looks good” and then flagging the gap in a separate email is not Radical Candour. It’s Ruinous Empathy at the senior level — and it’s actually disrespectful, because you’re protecting yourself from discomfort at their expense.

The receiving end

This framework also changed how I ask for feedback. The question I used to ask — “do you have any feedback for me?” — is almost designed to produce a meaningless answer. Nobody wants to think on the spot about how to critique you.

The question that gets useful answers is: “what’s one thing I could have done differently in that meeting?” Specific. Bounded. Easier to answer honestly.

The qualification

Radical Candour is not a licence to say whatever you think. The “care personally” axis is load-bearing. The framework requires you to have done the relationship work first — to have shown genuine interest in the person, their development and their context. Without that, challenge without care is just blunt criticism.

If you haven’t read the book, it’s worth reading before you try to apply the framework. The nuance matters.

Nobody hands you a manual when you step into your first big portfolio role.

You get a spreadsheet, a room full of competing priorities, and a calendar full of stakeholder meetings where everyone wants their project to be the most important thing happening in the organisation.

I learned most of what I know about portfolio management the hard way. After years of governing portfolios from £10m to £30m+, I can tell you that the hardest parts are never the ones people warn you about.

Here is what I wish someone had told me on day one.

1. You are not managing projects. You are managing people with agendas.

Every methodology you study, weighted scoring models, strategic alignment frameworks, portfolio prioritisation matrices, assumes that decisions will be made rationally. They will not.

The minute you publish a prioritised list of projects, someone senior will appear in your inbox asking why their initiative is ranked fourth. Not because fourth is wrong. Because it is theirs.

Portfolio management is political navigation as much as it is project governance. The weighted scores are your evidence. They are not your weapon. Learn to present them as a shared tool, not a verdict.

The leaders who do this well are not the ones with the best frameworks. They are the ones who understand what each stakeholder actually cares about and can speak to that directly.

2. The hardest decision you will ever make is killing a project that everyone loves.

Zombie projects are real. They are projects that no longer make business sense but continue to consume resources because too much political capital, emotional investment, or sunk cost sits behind them.

Nobody warns you that your job will sometimes require you to be the person who says: this needs to stop.

It will feel like admitting failure. It is not. Stopping a project that is no longer delivering value is one of the highest-value decisions a portfolio leader can make. Every resource freed from a zombie project is a resource available to something that actually matters.

The way to make this easier: make the decision criteria visible and agreed before a project gets into trouble. When everyone has signed up to the same definition of “this project should continue”, the conversation about stopping becomes a data discussion rather than a personal one.

3. Green status reports are the most dangerous thing in your portfolio.

You cannot know the details of every project personally. You rely on the people running them to tell you the truth about how things are going.

Most of the time, they will not. Not because they are dishonest. Because they are optimistic. Because they believe they can fix it. Because they do not want to be the one who raised the red flag.

The most expensive risk in a large portfolio is a polite team.

Develop a radar for when the data is hiding the reality. Ask questions that go beyond the status report. When three projects are green and you know they share a key resource, dig in. When a project has been amber for six weeks with the same mitigation action, push harder. Your job is not to read the dashboard. It is to understand what the dashboard is not telling you.

One practical fix: make it safe and normal to raise risks early. Celebrate the team that spots a problem in week three rather than week ten. Culture shapes what gets reported.

4. Saying yes to everything is the fastest way to deliver nothing.

Early in my career I believed that hard work could overcome resource shortages. I was wrong.

I said yes to too many projects, assuming we could always find a way to make it work. What actually happened was that nothing was done well or on time. Projects suffered from resource shortages. Deadlines were missed. Quality dropped. And the team burned out trying to keep pace with a portfolio that had been filled without any real consideration of what it would take to deliver it.

The busy fool trap is real. Doing everything means excelling at nothing.

The most important word in a portfolio leader’s vocabulary is no. Not no to ambition. No to projects that cannot be resourced properly, that are not aligned to strategy, or that exist primarily because someone senior wants them to.

You are a steward of organisational resources. Act like one.

5. Your BAU work will eat your portfolio alive if you let it.

This one took me longer than I would like to admit to get right.

Business as usual work, the maintenance, the support, the keeping the lights on, is invisible until it is not. It does not appear in most portfolio dashboards. It does not get discussed in most portfolio reviews. And it consumes a significant portion of your team’s capacity every single week.

Define clearly what BAU means in your organisation. Separate it visibly from your change and transformation work. Understand what proportion of your total capacity it consumes before you commit to anything else.

And keep your portfolio simple. One intake channel, not nineteen. A small number of meaningful categories, not a taxonomy that requires a glossary to understand. Every column in your portfolio view should earn its place. If a stakeholder cannot act on the information in a column, remove it.

A portfolio that is simple, visible, and honest is more valuable than one that is comprehensive and impenetrable.

6. The things that save you: one playbook, one source of truth, one way in.

After years of getting this wrong and then getting it right, here is what actually works.

One intake channel. Every request for new work enters the portfolio through a single defined process. No back channels. No “can you just squeeze this in”. One door.

One source of truth. One tool, one view, one place where the portfolio lives. Not twelve spreadsheets and a SharePoint site nobody can find.

A playbook. Written down. What BAU means, what change means, how things get prioritised, what each column represents and why it exists. Visible to everyone. Reviewed regularly.

Clear definitions of done. Closed projects get archived. The portfolio reflects reality, not history.

None of this is complicated. All of it requires discipline to maintain. That discipline is your job.