Dealing with difficult stakeholders

Ever heard these statements?

“This is way down our priority list”

“We’re too busy”

“I just don’t see the value”

There will be many times when you’re trying to implement something that requires the buy-in of many people. It could be something that needs to be rolled out in parallel in more or less the same way across the organisation (like conducting training or implementing new reporting systems). It could be something that needs to be implemented more sequentially between departments, like the launch of a new product where each department has their specific role to play. 

In any situation, you will almost certainly come across resistance to this from people whose cooperation you absolutely need if you want to move forward. There are key people and not just in leadership positions who need to say “OK”. Leadership will delegate tasks. The person whose lap this lands in has as much say in what gets done and when as the leader has. 

When you’re dealing with a hard “No” it can be a really tough pill to swallow. So how can you deal with this? I’ll present some approaches that you might add to your repertoire of strategies. 

I’ll add a caveat that I’m assuming most folks we tend to work with are decent enough people, just trying to do their jobs and subscribe to the broader organisational goals. I don’t think what I’m proposing here will work much with people exhibiting outright negative traits or harmful behaviours. Sometimes these things might work, but there’s probably a different approach you’ll need to systematically bypass them or change plans completely if the problem is more serious. 

So assuming you’re dealing with a more regular situation, here’s what you can do. 

Realise that you too, are a “difficult stakeholder”

Yes indeed. From the point of view of others, you most certainly have had to say “No, sorry!”, to prioritise other things, to push back on a request. You’ve misunderstood the request, you’ve not seen the bigger picture, you’ve not “bought in”. 

If you can appreciate that the difficult stakeholder is probably acting much as you would given their priorities, resources, (lack of) knowledge and personal views then it becomes less of an emotional burden to muster the energy needed to get a result.

Whatever the reasons are for this person’s “No” – these are their reasons and to them, they are 100% legitmate and logical. It helps if you can respect that as your starting point. 

I believe this realisation helps lower some of the imagined barriers you might see when viewing their “No” as a massive wall you need to break down. When you can adopt the mindset of the other person, then the path from a “No” to “Yes” is more clear because it is much easier to appreciate why they may be objecting. This is powerful because now you can figure out how to alleviate their concerns or accommodate their objections.

With this mindset in place, the rest of the recommendations can be read or implemented in any order.

Take the path of least resistance – you also need wins

Especially early on, it might just be best to move on from a difficult stakeholder to one that is more aligned with what you’re trying to do. In all industries, enthusiastic supporters are embraced not just because they’re the easiest to work with, but they’ll give you some examples to work with and supporters tend to be more tolerant of you altering your approach or even making mistakes. Many appreciate that their input in the early stages is incorporated and shapes the project, which is why they are enthusiastic about it. 

On a more personal level, some early wins and having some supporters will be a great asset when you start working in more difficult circumstances. 

Timing – right place, right time

Be willing to be persistent. Sometimes, your previous request just came at the wrong time. If you’re willing to give a consistent message (even if packaged differently) and play the long game (as in, over many years), then you will overcome many objections this way. You should get some smaller concessions here and there, but the big change might only come much later – be prepared for that. 

My working theory is that the higher up in the organisation the objection comes from, the longer game you’ll need to play. Someone in an entry-level or mid-level position might only need 3 to 6 months to pass for them to be able to say “Yes, I can do this”. An objection from a Director might take years to overcome. I think that the higher up the org chart you go, the more the person has to lose from doing things they don’t agree with. On the other side, they also have a lot more information than you do and are prioritising things differently. Good Directors work on multi-year timescales, so be prepared to match that – both for supporters and detractors. 

Influence from peers and subordinates

For some people, the idea just has to feel like their own. Maybe they’ve just heard it expressed in a bunch of different ways from peers and subordinates and it slowly seeps into their thinking. When they buy in, it sometimes looks like a request that they initiated. To you it might seem like it’s exactly what you’ve been saying all along, but to them this might be a different take on it that’s much more valuable to them and they want to jump on board. They’ll probably ask for some changes to make it more suited to them. Accommodate them where you can, package them as they need it and jump on the opportunity. 

This approach works by having a long term strategy of your own coupled with consistent messaging. You seek out peers and subordinates and canvass them. You allow enthusiastic supporters to join in and keep advertising your successes. This lays a lot of the groundwork for some peer pressure to grow for the difficult stakeholder (“I really think your department will benefit from this”), and for positive “upward management” to happen from the subordinates who likely have much greater influence on the person than you do. 

Canvassing – get their agreement before you ask them

Canvassing is when you meet people individually and have private conversations with them. This is especially important when working with people higher up in the decision-making hierarchy who are blocking progress. These discussions will happen one-on-one or sometimes with one or two of their trusted advisors. The fewer people you have “from your side” the more open the discussion is likely to be because there are less witnesses to promises or statements made. How many people you bring along has a lot of factors to consider which I won’t cover here, but you are aiming for the least amount of people that gives the message that you are speaking with authority and decision making power, or at least strong influence. If you are the lead for the project, then ideally this is just you. 

This may sound counterintuitive, but in this setting you actually want your stakeholder to be able deny what they agreed to. This gives them the opportunity to be very open with you about why they can’t or won’t cooperate (even if you still need to read between the lines). If they repeatedly say one thing in private and then act completely differently publicly, then you’ll need to consider whether it’s worth canvassing, or start bringing more people to those meetings.  

The best outcome of canvassing is that you have a mutual understanding of each other’s positions and ideally an agreed way forward. When the time comes for more public commitment, then you get your “yes” or at least no objection. This is just the formality – you have already both agreed before going into the broader meeting.

This is a very time consuming exercise but in my experience, is often the only effective way to get things done because it has the crucial element of listening and understanding what that person needs for a win.

Understand their priorities

It’s unlikely that your proposal is getting blocked purely because they don’t agree with it. Often it will make logical sense and they may even whole-heartedly agree with it. Listen to what they have to say to you, what they say when they speak to others, when they make announcements or celebrate wins. All this info will paint a picture of where their priorities lie.

When you know the person’s priorities, it’s much easier to align theirs with yours. This is where you can employ your timing to coincide at the right moment, or influence peers and subordinates to work elements of what you want to do into their plans. 

The best win is when you both realise how it is that your priorities help support each other – and this often is a matter of repackaging your proposal for them (using different terminology, highlighting value gains differently etc) or changing your sequencing. 

Maybe your plan is to improve data visualisation in the organisation, but this stakeholder has much more to gain from automation and quality control – something you were only going to address later. Now you have something to work with and options for how to move forward become more apparent. Contrast this to spending years trying to convince this person why good data visualisation is important. 

Use their language

Don’t make the mistake of thinking that because you speak the same language that you understand each other. Especially as fields and roles become more specialised, the same words can have very different meanings and to make it more challenging, they’re evolving on their own trajectories. More often than not, just repackaging your message into their terms will give you huge gains. Talk to Legal about risk and liability. Talk to HR about retention. Talk to Operations about continuity. Talk to the CEO about competitiveness. Talk to Product about engagement. 

Make it easy for them politically

People are often not incentivised to change or take risks. If you’re asking for either, it helps if you can make it as politically palatable for them as possible. This one is the most difficult for me to articulate, but by employing some of these other approaches, you’ll get a sense for what this person:

  • Can agree to
  • Can’t agree to or;
  • What they can let move forward without an objection. 

I suppose it’s the last one that is the hardest to get right. In my experience, the best some people are willing to do is to not object to your plans. This gives them an easy way out if they can say they never agreed to it. What makes it difficult is that you might not feel you have a solid base to work from, but sometimes you have to accept this is the best you’ll get and just make a mental note that your planning might need to account for them backing out at any time. 

Sometimes, it’s just easier to speak to them

A lot can be lost in emails and instant messages. Language and rhetoric can escalate. People are copied in. People are discussing different things.  The recorded nature of text means messages are crafted (or not!) to reduce liability. It makes it more difficult for them to speak off the record (see Making it easy for them politically and Canvassing).

I had a recent example where I was dumbfounded by the “No” that I received. Back and forths over email weren’t going anywhere. I felt like we were speaking different languages. I invited them for a video call, explained my problem and why I thought I would get a Yes and was at a loss why I had a No. They explained their situation. In about 10 mins we understood each other. I had my Yes and it was no problem for them. Problem solved. 

Never ever say “I told you so” 

When they do finally agree, and especially if the benefits are as you predicted – don’t under any circumstances say “I told you so”. You might be craving the short term emotional satisfaction of replenishing your own energy that was drained because you had to really work to get the buy in, but don’t do it. You will likely immediately lose any good will you have just garnered and have probably made the next win impossible to get. 

Even if it was really hard to get this result and you feel like you were put through unnecessary trouble for it, don’t assume too much that the influence only went one way. You probably learnt at least as much as your counterpart did in this process. 

Some of my best professional relationships have been borne out of heavy debate and disagreement. “I told you so” in whatever way it’s delivered, shows you have no respect for the person’s point of view. Rather save your celebrations and high fives for your team – that’s a much better way to replenish your emotional reserves and you won’t come to regret it later.

If you’re managing a team – here’s how to help them

Dealing with a lot of difficult stakeholders can be detrimental to the morale of your team. I think the task of a good manager is to prevent the team internalising these struggles. Measure your success more frequently by your outputs, semi-frequently by your outcomes and only occasionally, or broadly, or loosely by the ultimate impact you are looking for. Focus more on how it is you’re gathering feedback, clarifying your messaging and “rolling with the punches”. Celebrate your wins and make sure there’s a safe space for people to vent their frustrations and compose themselves before going into that meeting, or writing that email. Recognise when strategies are working and provide plenty of time for providing input and a sounding board for people’ s plans.

Most importantly, encourage reflection and learn from each other so they have the same range of tools at their disposal as you do. 

A brief reflection of my own development

When I was a much younger lad – probably in my early twenties and just started working, I didn’t have this approach. I was much more gun-ho and when faced with disagreement, I felt that my logic and determination would make people realise that my way was right and theirs was wrong. Once I matured a bit (a lot!), I thought that if my plans were perfect and everyone said “Yes” then I would have the authority and buy-in to move ahead unobstructed. This was less wrong but still wrong. There is no perfect plan and even a “Yes” might actually be a “No” that you didn’t give the space to be heard. 

Now about mid-way through my career, my view is that long term plans are built on constantly shifting foundations. You need to deal with this situation in ways that preserve your energy for when you need it and replenish it whenever possible. The best gains and relationships often come from disagreements. The best outcomes come from those shaped with input of people who need to implement them. Some of your most “difficult stakeholders” might be your great allies in disguise.


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