Why is this team not accountable / meeting their deadlines?
It's often hard to diagnose why a team isn't meeting their deadlines. Here's what I look at with startup clients to see what's going on.
I check to make sure the motivation stack is reasonably well tuned; doesn't have to be perfect, but can’t have major blockages. So now I believe I have a motivated or team who isn't (yet) successful in delivering on time.
The three most common challenges are:
-- team/manager doesn't yet have the skill to lead accurate estimation & follow through This doesn't require more force or motivation, this is a skill that they need to learn. You can build that skill slowly with several iterations (estimate measure review learn), hire a manager who is already good at this and have them lead the team, or pair them up with a leader who is already reasonably good at this to guide them through a few times. But you're trying to bridge a critical skill gap.
Startups don't have the training & mentoring resources that larger companies do; if you are looking at a manager who lacks a key skill you need, assess how long it will take for them to learn it, and weigh that against the time/energy it will take to rehire for the role. For the most critical roles, you might have someone mentor /coach them while working on a pipeline of other potential leaders, so that you've got both options covered. If you are unsure, and already have a coach working in your org, they can probably help you assess this in a session or two and make a recommendation about how to move forward.
-- manager works hard but doesn't successfully pressure their team This manager may be conflict adverse, or lack the skill to create healthy conflict. I ask "Have you EVER seen them express an opposing viewpoint or asking in an authoritative way that people do things that might be difficult or less desirable?"
Roleplays work exceptionally well with these managers, if anything is going to work. Through the process of roleplaying asking a team member to work harder on something, you quickly unearth their own resistance, allow them to practice until they find language they think will be effective in making the request, and helping dealing with potential pushback. Some managers are not inclined toward this -- you may need to make it clear that doing this is a required skill they need to stay in a leadership role. Most managers can make good progress on this with skillful coaching -- if you have a manager who fails to do this successfully despite your best efforts, you may need to replace them. If you've been earnestly working on this for a month and have made scant progress, you will likely need a different leader.
-- work pipeline is too full, so everyone is spread thin and working on too many things at the same time. Your context switching costs are so high that you're getting poor value from your team by making everything a priority. Start reducing the number of simultaneous projects until you're getting better results. You will want to resist or ignore this -- it can be incredibly painful to realize your team can't do everything you're hoping for, but it's better to have a realistic picture of what's happening that you have a say in, than to let the team fail to deliver half of their projects, and never know what half won't be done. If you ask a team or leader if they are context switching too hard, they will usually give an accurate answer. More skillful leaders can context switch more frequently themselves, and self-regulate by pushing back when things aren't efficient, but knowing "how full is too full" is a skill unto itself.
The question to ask is "What percent of your work hours does your team spend working on things you knew you needed to do last week, and how much is ad hoc?" If the ad hoc work is greater than 50% (and the team is meant to do planned work, rather than manage incoming tickets), you're context switching too hard. You need to reduce the number of simultaneous projects, and/or simplify them. If you have the budget for it, you should likely either hire to build out the team (which will increase the workload temporarily but solve it long term) or find a contract option to do some of the work.